3 "41 5 B 6 C
Be 9,012182 10,811
6,941 12,011
6EPV1nnV1111 KOBa eBCKaH H., -. b yrnEPO
11 M 12 14 Si
g n. n:J
PEMHV1111
2
47,88
!C
ME,lJ,b rEPMA',.
37 Sr y Zr
88,90585
),4673 87,62
CTPOHLjV1111 IIITTPV1111 LjVl r
/.(J1R
noi)zomo6KU
K 6bmYCKlIbl.M U
6cmynUmeJlbllbl.M
3K3a.Mella.M
 I g o r ' 4 1
g 12 1 ..0 11l !
- E6PO KA,lJ;MIVI
551f3.n A !e F r
n,9054  137, 327 1
6API1V1
u 80
f-"'-
200,59
nOTO
87
Ip

B03Hi1KHOBEHi1E OprAHW-JECKO Xi1Mi1i1
KAK HAYKi1. (1807r. .6epl..!.em1Yc)
IIepBble KJIaCcIHjJIIKaU:IIII (no npOIICXO)l():(eHIIIO):
BellteCTBa
(U3YIfaJlUCb pa3iJeJlbHO)
M"Hepa 1" OTH..e
paCTMTenbHble
it EeplIeJIMYC: "BeIl(ecTBa, rrOJIyqaeMble fl3 opraHfl3MOB
(pacTHTeJIbHoro H )KHBOTHOro rrpOHCXOJK,l(eHlUl) - opraHM-
qeCKMe, HaYKa, HX Ii3yqaIOIl(aJI - OpraHMqeCKaD XMMMD."
no EeplleJIMYcy OpraHHqeCKHe BeIl(eCTBa HeJIb351 rrOJIY-
qllTb B JIa60paTopHII, KaK HeOpraHllqeCKHe. OHll C03)..\aIOT-
CD opraHM3MaMM rro)..\ BJIIUlHHeM """M3HeHHOM CMJIbI".
BHTaJIllCTllqeCKOe Y'IeHHe 0 ")KH3HeHHOll CHJIe" Onm60qHO
( OT JIaT. vita - )KH3Hb)
B 1824 r. HeMeU;KHllxHMHK <1>. BeJIep (yqeHHKEepu;emryca)
cMHTe3upOBaJ1 M3 ueOpraHUqeCKUX Bell(eCTB Il(aBeJICBYJO
KHCJIOTY.
1828 r. - MOqeBI:IHY (<I> .BeJIep )
1845 r. - YKCYCHYIO KllCJIOTY (A.KOJIb6e)
1854 r. - )KlIpbI (M.EePTJIo)
1861 r. - caxapHcTbIe BeIl(eCTBa (A.EYTJIepoB)
3
I

BelLleCTBa Op....aHW.mCKL1e L1 HeOp....aHWmCKL1e.
COCTaB L1 HeKOTOpble CBOMCTBa
Op....aHL1'1eCKL1X BelLlecTB
Bew,eCTBa
/ 
OpraHW.feCKMe HeOpraHMl.feCKMe
Haps:lAY C APyn1MVl pa3H006pa3Horo
COCTaBa, H8T TaKoro
sn8M8HTaMVl Bce....Aa XVlM. sn8M8HTa,
COA8p)l(aT y....nepoA* KOTOpblCi npVlCYTCTBOBan
6bl BO BC8X B8Ll\8CTBaX
EOJIbllIIIHCTBO OpraHlI'IeCKIIX Bem:eCTB rOpIO'III, JIerKO
pa3JIaraIOTCH (t"=400-600°C), JIerKO E3amIOIIpeBpa-
m:aIOTC5.! .
YrJIepOll: B OpraHII'IeCKIIX Bem;eCTBax 06HaVVJKIIBaIOT
no 06pa30BaHIIIO OKCH,n;a YrJIepo,n;a (IV) - CO 2 , no
Bbr,n;eJIeHlIIO KonOTlI npii ropeHIIlI, no 06yrJIIIBaHIIIO.
OpZallUtJ.ecKaR. XUM.UR. -
amo XUM.UR. coei)ullelluu Yl.1lepoi)a;
XUMUR. YUle60i)OPOi)06 U ux npou36oi)llbIX.
* CO, C02, CaC2, H2C03 M ee COJIH COJJ:epJKaT yrJIepoJJ:, HO He
OTHOCHTCH K OpraHMQeCKMlVI BelI\eCTBalVI.
4

AOCTPYKTMBHble TeOpMM
TeopWI pa,mIKaJIOB (30 rr. XIX B. It I3epu,emIYc,
IO. JhI6MX, }[{. LIImm)
a) B COCTaB opraHWIeCI<HX BeII(eC113 BX0.l15IT pa.l1MKaJIbl;
6) pam-ma.Tlbl Bcer lJ,a rrOCT05IllllbI, He nO.l1BCprmOTC5I U3Me-
HemmM, rrepeXOlJ,5IT M3 OIII-Ioi-i MOJleKy JIbI B .l1PyryIO;
B) pal1HKaJIbI Moryr CYII(eCIBOBaTb B CBo6o.l1Hmr ElIJIe.
IIoHJITHe "pa.l1HKaJI" npO'lHO BOllIJIO B XIlMltlO. TeOpHJI
BnOCJIe.l1CTBIIlI OTBeprnYTa.
TeopWI THIIOB (40-.'50 IT. XL'C B. III. }Kepap, A.KeKYJIe
M.l1pJ
a) nee opraHWleCKIIe BCII(eCTBa - IlpOM3BOJIIIbie rrpocreihmIX
HeopraHWIeCKIIX - TIIIIa BOJ10pOJIa, BO.l1bl, aMMMaK<l M lIP.
nm BOAopoAa
R } CRa) CR.)
R R] CR,]
MeTaH 3TaH
R }
R °
nm BOAbl
CR3)
R]O
cnlllpT
Cffi )
CRa] °
npocTot1 3cj)[lJP
6) <POPMY.IIbT BbTpa)KaTOT He BHYTpeHHce
MOJIeKYJIbl, a crroco6bI 06pa30BaHlHI,
orrpe):(eJI5IIOT nee aTOMbl MOJIeKY.IIb!.
B) HeB03MO)KHO rr03HaTb CTpOCHHe BCII(eCTBa, Y Ka)I<JIOro
BeII(eCTBa CIDJIbKO <POPMYJI, CKO.llbKO cm rrpeBpaII(emID
CYII(eCTByer .
TeopHH n03BOJIHJIa KJIaccmlJHI[HpoBaTh OpraHH'leCKHe
BeII(eCTBa, npe.l1CKa3aTb M OTKpbITb HeKOTophle, oco6oe
BHHManne - XMMH'lecKHM npeBpaII(eHHHM, HO He MOrJIa
npOrH03IIpOBaTh, YKa3bIBaTh nYTH CIIHTe3a HOBhIX BeII(eCTB.
CrpOeIIMe
cBoj;icTBa
5

CBSl3b nOHSlTMM TeOpMM
XMMW.leCKOrO CT OeHMSI
(i)Jl.Jl Bew;eCmB JVlOJleKYJl.JlpH020 CmpOeHU.Jl)
KaqeCTBeHHbIH II
KOJIIfIIeCTBeHHbIll
COCTaB
CBOHCTBa
i
t
XMMW.leCKoe
CTpOeHMe
t
t
B3aIIMHoe
BJIII5IHIIe
aTOMOB
CTpYK'rypHruI
II30MepII5I
6

npeAnOCblnKM B03HMKHOBeHillSi
TeOpMM XMMMl.feCKOrO CTpOeHMSI
OpraHMl.feCKMX Bew,eCTB
"OpZaJiU'leCKaJi XUfilUJl JOJKem ceilliac K020 yzoaoo C6eCmU C Yfila. OHa
npeaCma6Jl.RB11lCfl ."tHe apeNyqlVl .i7eCOJ11-, 110Jl1-lbU;f, yallEUmeJlb1iblX eeuwi1,
6e3zpamtll1iOU tJGw,eu, U3 Kornopoti HeJlb3.fl 6b16pambC51, 'Kyaa 'He
OCeJlU6ae1UbC.Jl np01iU1<uymb It
(M:; HnCb"" <!> .Be",epa K it DepIje.'IIIYCY 18351'.)
OCHOBHhIC "npOTIIBOpC'lIIH" OpraHII'lCCKOH XII!\llIII:
1. MHoroo6pa3I1e BelILCCTB - 06pa30BaHO He60JIbIIImJ 'lI1CJIOM
3JIeMemOB;
2. KaJKYlILceC5I HecoorneTCTBI1C BaJIeHTHOCTI1 B OpraHII'leCKIIX
IJelILeCrnax - C3H8;
3. Pa3JIII'lHbIe <pI13I1'leCKIIe II XI1I\III'leCKIIe CBoIlcTBa
coe):(IIHeHIIH, I1lVIeIOIILIIX o):(HllaKoByIO I\IOJIeKy JI5IpHYIO
<POPMYJIY. C,H"D, - rJIIOK03a, <ppYK1D3a; CHwO -
6YUIJIOBbIH CIIIIPT, ):(II3TIIJIOBbIM 3<pI1p.
IIpC):(IIOChIJIKII B03HIIKHOBCHIIJI TCOpIIII:
1. Pa3BI1TI1e 11 YTBep}[{)J;eHI1e aTOMI1CTII'leCKIIX rrpe):(cTaBJIeHIIM
(c'be3):(BKap1Icpy3,1860);
2. YCTaHOBJIeIllie rrOIDITIIJI BaJIeHTHOCTII (3. <l>paHKJIaH)1, 1853);
3. IIOHJITIIe'leThIpeXBaJIeHTHOCTI1ymepo):(a (A. KeKyJIe, 1858);
4. l1.z1eII 0 coe):(HHeHIIII aTOMOB ymepo):(a B L\errII (A. KeKyJIe,
A. Kyrrep, 1857).
11 eJlOCml-lOU meopuu, nOdm6epJK.de1l.1IOU
3KcnepuMeHmOM, He cyw,ecm606flJlO.
7

TeoplllSi XIIIMIIILleCKOrO CTpOeHIIISI OpraHIIILleCKIIIX
COeAIIIHeHIIIM. OCHOBHble nOnO>KeHIIISI
(A.M. 5YTJlepOB 1861-1864 rr.)
, .
, .' ill
AiI:!'_
-:::
.. .
h, .
Jill t:- 'I
> =- ':" ,"

i ii H H H
_._ I I I
,... :. H-C-H H-C-C-H
' "/Ir!i H H H
-
1. ATOMbI 11 MOJIeKynbJ peanbHo cYIl(eCTBYIOT, AruMbI B
MoneKynax paCIIOnaraJDTCH He 6eCIIopH)J,O'lHO, OHH coe,!\11-
HeHbI ,!\pyr C ,!\pyroM B OIIpe,!\eneIIHOH IIocne,!\OBaTenbHOCTII.
/ , r
C ',i  r' r.
Wj"-.':(/
"- \ 
),t'r (
2, AruMbI B MOJIeI<yn:L'i: coe,!\11HHJOTCH B COOTBeTCTBHH C IIX
BaJIeHTHOCTbJO. YnIepo,!\ B OpraHH'leCKHX COe,l\I1HeHI1HX
'leTbIpeXB<l.JIeHTeH; em aTOMbI o6na,!\aJOT CBOHCTBOM
coe,!\HHHTbCH ,!\pyr C lIpymM B L\eIIH.
H H H
I I I
H-C-C-C-H
I I I
H H H
CH3 - CH2 - CH3
6
a
CTp)'KT)'pHa5! <JJOpM)'.a nOKa3bIBaeT IIOpHn:OK C08n:IrrleHI1H aTOMOB B
MOJIeKY Jle, IlX B3aIUvlOCB5I3b .n:pyr c .n:pyroM
(a - pa:JEepHyra}l, 6 - CDKpallJemlaH)
8

TeopHSI XHMHileCKoro CTpOeHHSI OpraHHileCKHX
COeAHHeHHH. OCHOBHble nOnO>KeHHSI
(npOAOmKeH\I1e)
3. CBollcma BeIl(eCTB 3aBIICHT He & M;C
TonbKO OT roro, ffi'OMbI KaKI1X
3neMeHTOB M B KaKOM tLO
KonWlecrne BXO)1HT B COCTaB
MoneKyn, HO M OT IIOCne)10Ba-
V>' ..;::i:'[ ...,,:
TenbHOCTM Coe)1MHeHMH >' 1. ..... r-, :".,  -"
rri '" . ',f' .:J.
aTOMOB B MoneKynax, OT '-"'"'-.;....,,-.:;: ... .-;,-... 3
B3auMHoro BnUHHIDI MX )1pyr
Ha)1pyra.
4. Pa3nMQHOe cTpoeHue rrpM O)1HOM U TOM )Ke COCTaBe U
OTHOC1-ITenbHOll MoneKynHpHoll Macce BeIl(eCTBa
o6ycnaBnMBaeT HBneHMe M30MepMil.
MaOMepbI - BeIlleCTBa, UMCIOIlUIe OJlliHaKOBhIH COCTaB MOJleKYJI
(OJJ:HY 1-1 TY Ke MOJIe]{y JI5IIIYIO q)OpJ'ryJIY) , HO pa3JIII'fHoe
XltMII'IecKoe crpoeHlIe II 06.rra,LJ,aJo1l(He II03TOMY pa3JI11'1HhIMli
CBOHCTBaMIi.
v CaeTaB Mr CTpoeHHe TKIm"C
n 4' C,R12 72 CR.-CH2-CR2-CR2-CR. +36,07
CR.
 fi;
,
1# ,.-. . C5H12 72 CR.- C - CR. +9,5
,
CR.
2 3aK 58
9

TeopHSI XHMHileCKoro CTpOeHHSI OpraHHileCKHX
COeAHHeHHH. OCHOBHble nOnO)f(eHHSI
(npOAOmKeH\I1e)
«  ,,£lD t
. . ...
j.
5. XI1MWleCKoe C'TpOeHl1e MOJleKyJl rr03HOBaeMO. DHO MmKeT
6bITb yCTaHoBrreHo rrYTeM CIUne3a 113 Bell\eCTB H3BecTHoro
COC'TIlEa H CTpOemUI, rrpil il3Y'IeHHH CBOMCTB rrOJIy'IeHHOI"O
BemeCTBa H rrpOJ1YK"TOB ero rrpeBpall\emm.
.lI:aJIbHeHllIee pa3BMTMe TeOpMM:
1. 1II3y<Icllne npocTpaHCTIJeHIIOrO paCnOJImKem!5I aTOMOB -
crepeoxmnm;
2. 1II3Y'IeIlHC opraHH'lecKHx nelljeCrB c rrpHMeHeHHeM
cJJIeKTpoHllOro Y'lelll15I crpoeHHJI aTOMa.
"Bp51iJ JlU .\IO,atD lta3fJamb iJpyzY1{) mnpaCJlb HaYKU, fJ Komop011
eiJZlNCllmeUHa51 11IeOpU51 3am.1NaJla 6bl mCl1WC iJO..\11.LHupYlow,ee U
onpeiJeJl5l1{)w,ee KYpC nOJlOJlCCHUe, lWK meopU51. ClIIpOeHlI51
A.1Vf.EymJlcpoBa fJ opzaH1.1'leC1Wl1 XliNUU. Eo.we c11Ia Jlcm OHa
CJi./fJlwrn CIIICpJ/{HCN pa36Ul11U51. U paCl\Bcrna 3111011 HaYla.l. "
(aKaA. A.HJ-IecMc5IfloB)
10

AnropMTM nOMCKa B03MO>KHbIX M30MepOB
anKaHOB (M30MepMSI yrnepO,AHOrO CKeneTa)
aJII'OpHTM rrOHCKa rrpHMep
I. PaCIIOJIO>KllTb Bce me CTb 3amIcaTb c:jmpMYJIbI B03MOJRHbIX
aTOMOB yrnepO,l1a JIIlHeHHO ):1pyr H30!VIepOB reKcaHa CUH14*
, 2 , , , ,
'Ja ):1pyroM II rrpOHYMepOBaTb llX; 1- C - C - C - C - C - C H30MepMl
2. Yl<OpOTllTh YDlepO):1HYIO uerrb
, , , , ,
lIa OllllH aTOM II rrpllCOe):1HIlliTb 2. C-C-C-C-C 1130Mep ]\&2
" OTOpBaHH:bliI lI aTOM KO ,
C
II ropOlvlY aTOMY yrrrepO):1a;
, , s , ,
3. II Cpe):1BllH)'Tb 1I0TopBaHHbIll" 3. C-C-C-C-C IISOMep NE3
aTOM K TpeTheMY; C
, 2 , , ,
4. IJepe):1BllHYTb II oTopBaHHbIHII 4. C-C-C-C-C
,
aTOM K 'IemepTOMY M01KHO, Ho C
IIY>KHO JIll? ( cpaBHllTb C 15 4 S 2 I npu HYJlWpaljUli
C-C-C-C-C I{enucnpafJa
nYUKTOM 2); C na,!eoo
H30Mep N2
. nOTopBaTb" erne O):1llH aTOM C
ymcpo):1a II rrpllCOe):1eHllTh 06a , " , ,
5. C-C-C-C M30Mep M4
KO BTOPOMY; C
h.06a lIoTopBaHHblx" aTOM a C C
IIpncOe):1eHllTb K TpeTbeMY , 2 " , , , " ,
6. C-C-C-C C-C-C-C
a I'(JI'vIY yrJIepoJJ;a B [(errll ,
C C
(cpaIJHHTb C rrYHKToj\I 5); II30Mep ]\&4
L , , ,
1. " (hopBaHHble " aTOM!.I npll- 7. C-C-C-C H30Mep M5
COC1ICHllTb KO BTOpOMY II C C
I PCTbCMY aTOMlli\1ynlepO):1a. "Y reKCflHa llJITb B03MOJICHbIX 1I30MepOB
I: cJJOpJlllYJlbt COCmaB.fteHbl Ha OCH06e YZJlepofJuozo CK£Jl€ma.
/(.I1J1 /IlULUCaHlUl cmpYKmypHblx rjJop.lI1.YJl rLe06XOallxw 80nllcamb Bo8opo8.
II

Knacc.....«I>.....Ka.....SI X.....M.....'IecK.....X peaK.....ii1,
T.....n.....'IHbIX AnSI opraH.....'IecK.....x coeA.....HeH.....
no THny XHMHqeCKOrO npeBpaeHHH
peaKlfuu 3aMeUfenuJI, COrrpOBO:JK,!\alOTC.H o6pasoBaHMeM
HOBbIX KOBarreHTHbIX CB.HseH rrpM saMeru;eHMM O,!\Horo
aTOMa (MJIM rpyrrrrbI aToMoB) Ha ,!\pyrMe aTOMbI MJIII
rpyrrIIbI.
H
I
H-C-H + Cb
I
H

H
I
H - C - Cl + HCI
I
H
pealClfuu npucoeiJunenuJI, (cMHTesa) COrrpOBO:JK,!\alOTC.fl
o6pa30BaHIIeM HOBbIX 6 (cMrMa) - cB.HseH sa CqeT pa3pbIBa
1t (rrM) - cB.HseH.
CH2 = CH2 + HBr
 H - CH2 - Clli - Br
pealClfuu pa3l/.0:HCenUJl, cOrrpOBO:JK,!\alOTC.H o6pasoBaHIIeM
HOBbIX 60JIee rrpocTbIX rro cocTaBY MOJIeKYJI.
H H
I I
H-C-C-H
I I
r,------
,J:! _ _ 9J!:
H2S0'(K)

CH2 = CH2 + H20
12

Knacc.....«I>.....Ka.....SI x.....M.....'IecK.....x peaK.....iIi,
T.....n.....'IHbIX AnSI opraH.....'IecK.....x coeA.....HeH.....iIi
no cnoco6y paaphlBa CBlla«
peaKlfuu C o6paao6anueM paiJuKalw6 COrrpOBO:IK,n;aIOTCH
CHMMeTpJPIHLIM paapLIBOM CBHaH (roMOJIIfTIfTleCKIf:H
paspbIB) OGru;aH 3JIeKTpORRaH rrapa ,n;eJIIfTCH Me:IK,n;y
aTOMaMIf, oGpasYH pa,n;IfKaJIbI.
H
H:rH
.
H
..
H C.
..
H
+
.H
MeTaR
pa.I\lmaJ]
MeTHJI
pa.I\HRaJ]
B°.I\°P°.I\
CH4 --.CH3 +.H
peaKlfuu C o6paao6anueM uon06 COrrpOBO:IK,n;aIOTCH
HeCHMMeTpH'.IHLIM paapLIBOM CBHSH (reTepOJIIfTIfTIeCKIf:H
paspbIB). OGru;aH 3JIeKTpOHHM napa OCTaeTCH y o,n;Horo
aTOMa, oGpasYH IfOHb!.
H H +
.. ..
H C: CI . H C + :CI
.. ..
H H
MeTHJ]XJIOPH.I\ MeTHJI - XJIIII'''/\
RaTHOR 111111011
+
CH3CI -- CH3 + CJ
13

KnacclIIIIIKa4111S1 yrneBoAOpOAOB
YI'JIeBO,l\OpO,l\bI
all;HKJIH'IeCKHe
(aJIII(jJaTII<IeCKIle)
MOJIeKYJIbI COp;ep>KaT
HeaaMKHYTbIe (OTKpbITbJe)
L\errii aTOMOB yrJIepo,L\a.
IJ;errii Moryr 6bITb rrp.!IMbIMII
II pa3BeTBJIeHHblME
CH,-CH2-CH2-CH3
6YTBH
8TllJIeHOBbIe
(aJIKeHbI, OJIeqJIIHbI)
CH2CH-CH2-CH3
6YTeH-1
p;neHOBbIe
( aJIKap;IIeHbI)
CH2=C-CHCH2
I
CH,
2- MeTJIJI-
6YTB.zjHeH - 1,3
au..eTllJIeHOBbIe
(aJIKIIHbI)
CH3-G,=C-CH3
6YTHH - 2
II;HKJIH'IeCKHe
IJ;errii IIa aTOMOB yrJIepo,L\a
aaMKF(YTbI B KOJIbL\a
(L\IIKJIbI)
apOMaTR'IeCIIe
(apeHbI)
MHorOH - OP;HO.!I-
,L\epHbJe ,L\epHbJe
00 @
Hae])TaJIIiH 6eH30JI
a.rrIIL\HKJIH'IeCKHe
L\IIKJIOrrapa<pIIHbI
(L\IIKJIOaJIKaHbI)
H,C-CH2
I I
H2C-CH2
L\HIUI06y'raH
L\IIKJIOOJIeq,IIHbI
(L\IIKJIOaJIKeHbI)
CH2
H2C O CH
H2C I CH
CH 2 l.\HKJIOreKCeH
14

MeTaH. CbIll3111"1eCKllle CBOMCTBa.
CTpOeHllle MoneKynbl
CH4
i, '\  H B BOl.\e,
JIer-qe B03l.\yxa, T KIIn =-162"C
MeTaH
60llOTHbIH ra3
Mr=16
63pbt600nacen
,!(Ba "npOTHBOpeqHSI" B CTpoeHHH MeTaHa:
1. BarreHTHocTb ymepo,lJ,a paBHa '-IeTblpeM ...
B HarrIIl:JIIII TonbKO 2 BarreHTHblX 3neK'rpOHa
BLIXO)J;'" B036YJK)J;eHHoe COCTOHHue yrJlep0)J;a.
C 2S 2 2p 2 -. C* 2S 1 2p 3
CLIII:J DJIIIJ
n=2 [IT}................ ../ n=2 OJ
S p S p
2. B MoneKyne Bce l:JeTblpe CB1!3II O,lJ,IIHaKOBbIe ... no
TeopIIII ... omra ss CB1!3b II TpII sp CB1!3II.
BbIXOA - Sp3 I"H6pHAH3aQHSI
ZU6PUOU3111fILR - U3.llelle1-lue qJOp.=ttbl U 31-1Cp2UU pa3Ru"t/JibLT Op6U111Wteii
Oi')1-1070 QmOMO, npUGOORlljee K 06plHOCOHliIO OOUHOKUCblX (zu6puo-
IIbIX) op6umtL,eil.
15

sp3 r I,16pI,1AI,13au.l,1S1
Sp3
("IIITaeTG! 3C - TI3 - TpM)
Is + 3p  4 Sp 3
0 ",
':".-
S
+--+ E+
 - 
Px Py pz
I 09°28'
'leTblpe Sp3 06pHTaJlH
L109°28' - Lmax YAaneHHJI 3apmKeHHbIx 3rreK'rpOHHbIX
o6rraKoB
A(C - C) COCTaBJmeT 0,154 HM
TeTpaSAP
oQ)-
6 (cHIMa) - CBJI3b
(nJlOTHOCTb3J1eKTpOHHoro
06JlaKa nla. B)J;OJU, OCM,
,
coe}JJH-UlIOeH $I.IJ:pa aTOMOB)
16

AnKaHbl
(II pedeJl"b1ibte UJlU 1iaCbIWpi1ibte YZJleBodopodbl, naparPU1ibl,
JKUp1i"ble UJlU a J7UrPamu'teCKUe COedll1ie1iU.fl)
I I COeJ\l1neHHH ymepoJ\a C HOJ\OPOJ\OM, B
C H MOJIeKYJIax KOTOpblX aTOMbI ymep o l1 a
n 2n+2 COeJ\l1neHbI Me>KI1Y C060H OJ\Hl1apnOH
. (6-cI1IMa) CBH3b10, a Bce OCTMbHble Ba-
neHTIIOCTU HaCbll.QeHbI aTOMaMH BO.o;OpO;:J:a.
CoeOUHeHUfl, CxoOHble no cmpoeHUIO U XUMU'leCKUM ceOUCmeGM U
01l1JlU'la1OUjueCfl opyz 0111 opyza Ha OOHY WlU HeCKOJlbKO zpynn CH"
HG3blealOm ZOMOllOZUMU.
rpynna CH2 - rOMOJIOrIIQeCKa5I pa3HOCTb.
CbLil3Li1"1eCKLile CBOMCTBa
C,-C 4 - ra3bI, C,-C'6 - )KI1,L\KOCTH, > C'6 - TBep)J,bIe BemeCTBa, B BO)J,e
HepaCTBopHMbI, MorYT paCTBOp5ITC5I B opraHH'IeCKHX
paCTBOpHTemIX. TKllII Hepa3BeTBJIeHHbIX . . BbIme, TKlIII
pa3BeTBJIeHHbIX ---< RI-DKe.
TKHII reM BbIme, 'IeM > Macca MOJIeKYJThI.
o
,
J:f"
o
o
mapOCrep)KHeBa5! MO)J,eJIb MOJIek1'JIbI n-IIeHTaHa
CR,
/ "-
CR3
CR2
/ "-
CR2 CR,
3I1naroo6pa:3Ha5! r(enb Mo)](eT npIlHilMaTb pa3JI11'lliLIe
IIpOCTpaHCTBeHHbIe <jJOpMbI. ATOMbI B MorreKyrre CB060)J,HO
Bpall(aIOTC5[ BOKpyr xm.mqeCKHX CB5!3eH
Sp3 rI16pIID,I-I3aIU-l 5J LI09°28' A(C - C)- 0,154 HM
17

M30Mepbl M rOMOnOrM
IIoHHTue
1I 30.Mepbt
rOJIWJlOZU
KaqeCTBeHHbIM KOJIll-qeCTB€H- XllMH'tleCKOe XUMH'rJeCRHe
COCTaE HLIH COCTaB CTpOeHEe CBOMCTBa
oi}UllalLOBblU oi}UllalCOBblU pa3JlUlU-We pa3JlUlUlble
Oi}U1-laK06blU paSJlUlUlblU cxoDlloe CXOOHble
:2
u
. J
:i3

C,)
"
:i3
c3
P1
 C,) 
:r: I :r:
C,)-C,)-C,)
I

:r:
C,)
P1
C,)
I
::E
" C,) 
:r: I :r:
C,)-C,)-C,)
I
::E
C,)
rOMOJIOril
P1
C,)
I 
:r: :r:
C,)-C,)
I
P1
C,)

:r:
C,)
I
::E ::E
C,) C,)
I I
P1 "
:r:
C,) C,)
I  r  :5
:r: :r: :r: :r: e.
C,)-C,) C,)-C,)
r r
::E " 
:r: c
C,) C,) 
rOMOJIOril :::
::E
C,)
I
::E :Ii
C,) C,)
I I
::E ::E
C,) C,)
I I
:Ii :Ii
C,) C,)
I I
::E :Ii
C,) C,)
I 
::E :r:
C,) C,)
::E
C,)
" I
"
:r: :r:
C,) C,)
L I
::E :r: ::E
C,) C,) C,)
I  I
::a " "
:r: :r: :r:
C,) C,) C,) C,)
rOMOJIOril
18

AnKaHbl (Hepa3BeTBneHHOrO
CTpOeHMSI) M anKMnbl
MOJIeKYJI5IpHa HaSBaHIIe Pa,L\IIKaJI HaSBaHIIe
<j:>oPMYJIa pa,L\IIKaJIa
CnH2n+2 /'-. CnH2n+l /'-. /'-.
an aH -----+ HJJ
CH4 MeTaH CH3 MeTIIJI
C2H6 3TaH C2H5 3TIIJI
C3H8 rrporraH C3H7 rrpOrrIIJI
C4HlO 6YTaH C4H9 6YTIIJI
C5H12 rreHTaH C5Hn rreHTIIJI
C6H14 reKCaH C6H13 reKCIIJI
C7H16 rerrTaH C7 H15 rerrTIIJI
C8H18 OKTaH C8H17 OKTIIJI
C9H20 HOHaH C9H19 HOHIIJI
ClOH22 ,D;eKaH ClOH21 ,D;eKIIJI
CUH24 YH,D;eKaH CUH23 YH,D;eKIIJI
. . . . . . . . . . . . . . . . . . . .
C20H42 3HK03aH C20H41 3HK03IIJI
19

HOMeHKnaTypa
XUMU'IeCKaH HOMeHKJIaTYpa - no CHCTeMa £I.1oPMyn H
Ha3BaHHH XHMIfl-IeCKHX BeIIJ,eCTB. OHa BKJIIO'-IaeT rrpaBlma
COCTaBJIeHHH £I.1oPMyn H Ha3BaHHH.
PaU;UOHaJIbHaH HOMeHKJIaTypa
YrneBO,D;opO,D;bl paCCMaTpHBaIOTCH KaK npOU3BO;:J:Hble
MeTaHa, y KOToporo OlUm HnH HecKonbKO aTOMOB Bo):(opo):(a
3aMeIIJ,eHbl Ha pa):(HKaJIbl.
R
1
R -;6:- R
-,-
R
R
I
r -I
CR3 -I C 1- CR3
-1-
CR3
MeTaH
TpHMCTIIJIMeTaH
CR3
I
r -I
CR3 -I C 1- CR2 - CR3
-1-
CR3
TpHMeTIIJI-3TJiUIMeTaH
20

HOMeHKnaTypa >KeHeBCKaSi
IIInlll CIllCTeMaTM"IeCKaSi
PeKOMeH,l:\OBaHa HIOTIAK (Me)K,l:\YHap0,l:\HbIH COlO3
TeOperJIl-!eCKOH II rrpIIKJIa,l:\HOH XIIMIIII)
II106a51 pa36em6JleHHa51 l1enb paCCAWmpU6aemC51 KaK
HOpMWlbHa51, 6 KOmOpOU amm.lbl "H" 3aMell/eHbl Ha paiJuKaJlbl.
1. BbI6HpalOT HaH60nee p;nHHIIYIo (rnmJHYIO) IICIIb;
,--------------------
13 4 5 6 7 I
CR, -ICR - CR, - CIh - CR, - CR '- CR2 - CR,
I
I I .-------------, I
I 2 I I 8 L - 9 - - - 10- - I
:CR2: : CR, - CR2 - CR,'
111 I ------------1
'CR,'
L _ _.I
3 - MeTIIJI - 7 - 8TIIJI).\eKaH
2. I-IYMepYIOT aTOMbI yrnepoAa B rnanIIoit DeIHl, na'IHIIa5! C TOro IWHDa,
K KOTOPOMY 6mDKe pap;HffiIfl. (ecnH 3aM€CTI1TeJIll Ha panHbIX
paCCTQ}!HIIJIX, TO Hyl'IepOnaTb C 60Jlee pa3neTBneilIIoro KOHDa);
3. Ra3BaHIIe CTpOHTCJI B cneP;YIolI(eii nOCJIe.n:onaTeJlbI-IOCTlI: CI-IatIaJIa
)'K'ISbIBaeTCJI WI<ppa, 03Ha'laIOlI(a5I HOMep aTOMa yrnepOl1a B rmumoii
lerrn, Y KOTOpOro IIMeercH pa.n. HKan (n<-1t.HlIlaH C npocTeihrrero) ,
3aTe:r.r - I-Ia3BaHne pa.znmaJIa H: Ha3naHliC rJ£aB1!OII J.enH;
4. ECJIH cop;ep)I{lITcJI HeCKOJlbKO op;IIHaKOBbIX paWII<aJIOIJ, TO nepep; IL,(
Ha3BaHHeM YKa3bIIJaIOT 'lHC.OIJYIO npHCTaI31<y (l1H-.l1na, TPH-TPH,
TCTpa-'IeThIpe), a IIOMepa pa.n.IiKanOIJ pa3p;e!UllOT 3aIUlTbIJ'.n-I.
CR,
;-"7 - - - "6 =- - - "51- - -:.. - - - -3- - - -; - - - -1-- 1
,
'CR, - CR, - C - CR, - CR, - CR - CR,.
,
,_________l___________J_____
CR, CR,
I
CR,
2,5 - ).\IIMeTIIJI - 5 - 8TIIJIrerrTaH
21

Onpe,AeneHlo1e KaeCTBeHHOrO COCTaBa
OpraHIo1eCKIo1X BellteCTB (1O.J11016Io1x 1831r.)
Ka'leCmBennbu1 COCmaB IIOKa3bIBaeT, M3 aTOMOB KIJEMX
9JIeMeHTOB COCTOMT MOJIeKYJIa BelI\eCTBa.
KOltU'leCmBennb£ii COCmaB IIOKa3bIBaeT, KaKOe <[MCJIO
aTOMOB Kam,n;OrO 9JIeMeHTa 06pa3yeT MOJIeKYJIY BelI\eCTBa.
COBpeMeHHLlH MeTOp; Onpep;eJIeHHH
yrJIepOp;a " BOp;OpOp;a:
AOpraHM<[eCKMe BelI\eCTBa OKMCJI.HIOT OKCM.n;OM Me.n;M (II).
o CxH y + CuO to) Cu + C02! + H20
K
C - C02 Ca(OH)2 + C02 = CaC03i + H20
ll.30eCmlW6a,f/, 6e.J/;HU
60iJa
a
9 H - H20 CUS04 + 5H20 = CUS04 . 5H20
6Jl-eiJHo-20Jly6oi!
.flpH:O-CUl-tUU
a
T Hal (XJIOp,6pOM) - npo6a EeHJILIDTeHHa (1872 r.)
HarpeBaHMe Bern;eCTBa C OKCM,l\OM
Me,l\M (II) B IIJIaMeHM rOpeJIKM
A a) Bern;eCTBO cropaeT
h 2C2H4Cb + 502 = 4C02 + 2H20 + 4 HCl
e
C 6) XJIOpOBO,l\OpO,l\ pearMpyeT C OKCM,l\OM Me,l\M (II)
CuO + 2HCl = CuCb + H20
T
B) 06paaOBaBIIIa.!IC.!I COJIb OKpaIIIIIBaeT nJIaMH B
B
aeJIeHLlH BeT
o
22

XiotMiotLieCKiote CBOCTBa anKaHOB
HHepTHbie Bell4eCTBa. CBHSH C-C H C-H rrpO"IHbIe, HHSKaH rrOJIH-
prI3yeMocTb ---7 peaKD;nn no rOMOnnTllY:IecKOMY pa3pbIBY CB.HSeH.
I. OKlIc.eHlIe
i) ropeHHe (Bbli1eJIeHile 60JIbliloro KOJIWIeCTBa TeI1JIOTbI Q)
CnH2n+2 + ( 3n;1 )02 = nC02 + (n+l)H20 + Q
n=l CH4 + 202 = C02 + 2H20 + Q
2) KaTaJII1TWlecKoe OKI1CJIeHl1e (kat - coell.. Mn)
[0]
CHs - CH2 - CH2 - CHs kat) 2CHsCOOH + H2O
YKCYCllaJllCUCllOma
II. Y CToii'lHBOCTb K lIeiiCTBHIO 06bI'IHbIX OKUCJIHTeJIeii
(KMnOI, Br2 BOlla) Ka'fecTHeHHaH p eaK U HH
CnH2n+2 He o6eCD;Be'lHBaeT Bn BO,l1Y II pop KMn04
III. KpeKHHT (pa3JIQ)KeHl1e IIpl1 e)
t
CH4 = C + 2H2
to
C4HIO = C2H6 + C2H4
amaH. :amUiIeH
IV. lf30MepuaaUIDI (C "C" :;" 4, to=100°C, kat AlCl)
t'
CHs-CH2-CH2-CH2-CH3  CH3-CH-CH2-CHs
n _ neHman AIC13 1 rLlo-neHman
CRs (2.MemuJl6yman)
V. PeaKl.\HH 3aMeemm
1) C raJIOreHai\Il1 CH4 + C12  CH3Cl + HCl
x.rwpucmbtil Memll.'l
h V - CBeT. e, UellHOll CH3Cl + C12  CH2C12 + HCl
CB06ol\IIOpa,'JHKaJIb- . . . . . . 't:."'tf!pllmbu JltimlJ/e1i.
HbIii MeXaIIH3N CHC13 + C12  CC14 + HCl
'leml>Lpexx.'lOpllCmbtU Y2JlepOa
MeXanU3m: Cb -7 CI. + CI.
CH. + CI. -7 CHs' + HCI
CHs' + C12 -7 CHsCI + CI.
H T.I1. 110 06phIBO
2) HH1'poBaHHe CI. + . CHs -7 CHaCI
t
(peaKUHH KOHO- CH4 +HON027 CH3N02 +H20
BaJIOBa) e, D. usom1W..J/ KUCJwma HumpOWmall
23

nony...eHMe anKaHOB
I. BbI,L\eJIHIOT U3 npUp0,L\HbIX UCTO'lHUKOB (npUpO,L\HblH U
nonyTHblH r33b1, HeifJTb, K3MeHHblH yrOJIb)
II. CUHTlITU'IeCKlIe cnoco6b1
1. II3 cOJIeH Kap6oHOBbIX KIICJIOT (peaKI!JUI ,Z:(roMa) npii to
f
CH3COONa(TB.) + NaOH(TB.) = Na2C03 + CH41
2. II3 raJIOreHaJIIWHOB (c1IHTe3bI BropI(a (a) II
BIOpI(a-fpIIHb.llpa (6))
a) CH3-CI + 2Na + CI-CH3 = CH3-CH3 + 2NaCI
3rJmp
6) CH3-CI + Mg  CH3-Mg-CI
peG1(mU6 I'pUllbJlpa
CH3-Mg-CI+CI-CH2-CH3CH3-CH2-CH3+ MgCb
3. 3JIeKTpOJlII3 no KOJIb6e
:JJIeKmpOJ/U3
2R-COONa+2H20  R-RI +2C021 +H21 +2NaOH
'- v J '- v J
Ha Ulw8e lLa lwmo8e
4. fa31I1l>IIIWI(II.II TBep,L\oro TOIIJIIIBa
Ni
C + 2H2 . CH4
P,t
5. CIIHTe3 1I3 CO II H 2  CMeCb aJIKaHOB
nCO + (2n+l)H2'CnH2n+2 + nH20
6. Pa3JIOmeHIIe Kap61I,L\a Al BO,L\OH
AI4C3 + 12H20 = 3CH41 + 4AI(OH)3
24

npMMeHeHMe anKaHOB
CBoC1CTBO YpaBHeHMe npMMeHeHMe
1. rOpeH"e CnH2n+2 +3n;1 02nC02 +(n+1 )H;20+Q TOnm1BO, roplO1.Jee AJl51
ABlllraTenei::1 BHyrpeHHero
cropaHIM.l.
2 .,0 nOnY'-leH(.1e OpraHt.1'-1eCKIt1X
2. KaTall"- CH 3 -CH 2 -CH 2 -CH s 1" CH 3 -C +H;20
"OH KcnOT (->CMC).
1.J6CKoe YKcyCHa
OKlllcn6HIII6 KMCJlOTa
3. KpeK"'Hr CH,->C+2H, 2CHrC2H2 +3H.. )].1151 flOnyLJ8HIII5I C8)/{!II (U1-
norpacpcKOL.1 KpaCKIII, pe-
C4H1()H6 +C 2 H 4 3I11Hbl), Bop,opOAa (aM-
MIII8K N), Henpe.o.eIlb-
HblX yrJ1eBOp,Opop,OB.
4. 1130Mep"- CH,,-CH,,-CH,-CH -a.;,-!>CH -a-I-CH -CH )].1151 YIlY"-lweHIII5I Ka'-leCTB
6eH31t1H8.
33L1,I1151 :2 1I1CI, 3. :2 3
CH,
5. PeaKl-\"H CH, + CI,-> CH,CI + HCI PaCTBOpIl1T8Jlb, CblPb€ AJl51
KpeMHIlli::1opraHIII'-IeCKIIIX
3aMew,eHlllfJ )(JlCpMeT3H npOAYKTOB, B npOItl3BOp,CT-
C ranoreHaMIII Be COJl5lHOVI Kl.1CnOTbl.
CH,CI + CI, --> CH,CI, + HCI PaCTBopLnenb, B npollls-
Bo,n,CTse BIIITaMIIIH8 A,
,Qt1XJlOpMeTaH (T",,=-96,7"C) B xonOAnb-
HOW TeXHIIIKe.
PaCTBOpIllT8J1b, AJl51
CH,CI, + CI,-> CHCI, + HCI nonYLJeH[I1f1 <ppeOHOB,
X.fJOp04>OpM TecpJlOHa, XJlopocpoca.
PaCTBOpIllTeJlb, AJI5! nOJlY
1..jeHItI5! cppeOHOB, AJI5! ra-
CHCI, + CI, -> CCI, + HCI WeHIi15i nJlaMeHIII, 06e3)KIII-
'1eTblpeXXIlOpI-10Tblj:i pli1BatOUee cpe.o.cTBo.
VmepqL\
CHG+ CI;2---7C 2 H s CI + HCI MeCTHa51 aHeCTe31115i.
xnop3TaH
6 B3aIllMO- nOJlYLJeHllle BOAopo.o.a,
AeL:1cTBllle NO pa3JlIII'-IHbIX yrJleBOAOpO-
CH, C BO- CH, + H,o,iiifc ? H, + c q AOB.
CL1HTE3ra3
A5IHbIM
napOM
3 3aK 58
25

LJ.Io1KnoanKaHbl (u.Io1KnOnapa$Io1Hbl, Ha$TeHbl)
C n H 2n
npep,enbHble yrneBop,OpOp,bl, COp,epJK8Me
38MKHYTble LlMKnbl M3 8TOMOB yrnepop,a,.
n3
LI"Kn d + anKaH
HOMeHKJla-rypa
H,C-CH, D
I I I1JliIl
H 2 C-CH 2
LJ,IIIKno6 yraH
;ymepoAHoro CKelleT
30Me p "SI KllaCCOB COeA"HeH"'"
... (anKeHbl)
 npoCTpaHcTBeHHa
(AIls:! ManblX LJ,It1KJlOB)
CH-CH, C
D WJlW Ii. H,
H,C CH,
MeTllln -IIIKnon ponaH
H 2 C-CH 2
J I
H 2 C-CH"
fiH,
H,C CH-CH,
EH,
Men1JlL..(t-1KnO-
nponaH
CH,=CH-CH,-CH,
6YTeH-I
HCH, CH,CH,
CH, H H H
TpaHC- LJ,I:IC-
1,2-AI:IMen1J1LJ,IIIKJlOnporlaH
CJ>"3W-leCK"e CBoi'icTBa
C,-C,- raSbl, Co-C,,- >K"AKOCT"', > C" -TBepAble, nllOXO P B H 2 0,
llerKO - B opraHW.leCK"'X paCTBOp"T811X.
T""TmBblwe, '-IeM y allKaHOB, 0611B.L\aIOT HapKOT"'eCK"'M ,Qei'icTB"eM.
X"Mw./eCK"e CBOHCTBa nOAo6Hbi anKaHaM
AllH MallblX I1"KnOB (c=3,4) xapaKTepHbl peaKI.\.... np..coeA"HeH"R C
pa3pblBOM 4"'Klla, An 6011bW"X I1"KnOB (c>5) - peaKI.\.... 3aMeLlleH"
 CH' 1" CH,- CH,- CH, H C  CH C 
+ Br z -+-- I I 2. U 2+ Br 2 ---+ H 2 U CHBr + HBr
H 2 C CH 2 Br Br H 2 C CH 2 H 2 C CH 2
nonY"IeH"e
1. peaKI1"H BIOPl13
2. JJ,erIllAPa.1pOBaHIt18 anKaHOB (e. KaT)
Haxo3ICoeuue B npupooe: (3 C(3cma(3e fteIjJmu., 3ljmpHbtX .maceJt
Ha36Wibl natjJmellbl (B.B. MaplC061illlwa)
26

3TlllneH (3TeH). CTpOeHllle MoneKynbl.
Sp2.-Lo16pLo1AIII3a,-"IIISI
t, 'l.\, 3 4YTb CnaAKOBaTbIVl,
nnoxo paCTBOpll1M B H 2 0
C 2 H 4
Mr=28
H.... c /H
C=C
r:/ 1t ....H
C* 2S ' 2p 3
n=2 IIIIIIJ

S 1S
ATOMbl yrnepoAa B MoneKyne 3TIt1neHa
06pa3YlOT ABOVlHYIO CBSl3b, HaxoAmc5J
B COCT05JHIt1It1 Sp2 rlt16plt1Alt13aLJ,1t11t1
CBSl31i1 HepaBHo.....eHHbl:
c (Cl1rMa) - 60nee npOI.jHa5J
n* (nl1) - nerl.je pBeTC5J, 60nee
peaKLJ,1t10HHOCnoco6Ha
+ 2P
.....:.
@ "'. +()(} ".' 0" + .>....
... ," . ...;. . ..:.:
.....-:0 ../, '" .....
\.
s
120'
TP" SP'
Op6L..nanll1
'A.(C=C) COCTaBJ7f/eT 0,134 HM
P z OCTa8TCfI
Herlll6plt1AHoL:1
a 6
CxeMa o6pa30BaHMf/
()" CBf/3ei!J (a) M 11: CBf/3ei!J (6) B MOJ7eKYJ7e 3TMJ7eHa.
OTCYTCTByeT cB060AHoe Bpaw,eHlt1e aTOMOB
BOKpyr ABOVlHOVI CB5J311.
*1t-CBf/3b - nJ70THOCTb 3J7eKTpOHHO,O 06J7aKa
max "Ha,n," M "no;:!," nJ70CKOCTbIO ()" CBf/3M (6oKOsoe nepeKPblB8Hl1e).
3' 27
P,
/

AnKeHbl (One4>MHbl, 3TMneHOBbie yrneBoAOpOAbI)
YmeB0,l10p0,l1bI, B MOJIeKYJIaX
KOTOpbIX I1MeeTCJI O,l1Ha ,l1BOHHaH
CBH3b Me)!(,l1Y aTOMaMI1 ymepO,l1a.
./'--. ./'--. ....------.-
aH ---7 eH II1flll1 IIIneH
HOMeHKnaTypa
1. B KayeCTBe maBHoC1 Bbl6111palOT l\enb, BKlllOalOll1Y1O ABOC1HYIO
CB3b, Aa>Ke eCllll1 OHa He caMa AllIl1HHa.
2. HYMepal\lI1 C TOro KOHl1a, rAe 6m1>Ke ABoC1Ha CB3b.
3. nOllO>KeHlI1e ABOC1HOC1 CB3111 YKa3blBalOT B KOHl\8, HOM8pOM
aTOMa yrllepoAa, nOC1l8 KOTOpOro OHa HaXOAII1TCSJ_
4. B HaYalle Ha3BaHII1 - nOllO>KeH1I18 60KOBbiX l\eneC1.
CH,
.....5- - -4- -31 -2- -1- - ...
: CH3-CH2-C=CH-CH
:3  MeTVinn8HT8H  2"
C n H 2n
pap,I1Kanbl
CH 2 =CH' BI1H\IIn
CH 2 =CH-CH 2 ' ann\lln
IIICKnlOlJeH\IIe: neHTaH-neHTeH \IIn\ll aMMneH
yrnepo,qHoro CKeneTa (C;;'4)
/ 1 2345 1 2:3 4
CH -CH=CH-CH -CH CH -C=CH- CH
3 2 3 3 :3
neHTeH-2 I 2 MeTlt1Jl-6yreH-2
_ _ CH 3
L130MepMSI _nOnO>KeHIIISI ,qBOIIIHOIil CBSl3111
12341234
CH 2 =CH-CH 2 -CH 3 CH 3 -CH=CH-CH 3
'\. 6YTeH-1 6yreH-2
KnaCCOB COe,qIllHeHIIIM (l\II1KnOanKaHbl)
1 2 3 4
CH 2 =CH-CH 2 -CH 3
6yreH-1
j
npOCTpaHCTBeHHaSi
H,C D CH,
H,C CH,
Ll"Y1KIlo6yraH
CH 3 , ./ H
C= C
1f..... ECJ1t.1 O.Q,HHaKOBble
1 2 3 4 / H TpaHc-....... CHfj 3aMecnnenlll HaXOAmcSl
CH 3 -CH=CH-CH 3 no OAHy CTOPOHY nOCKOCTI1
6YT€H-2 '\. H H ABOL1HOVI CBSl3111. aTO -
'c = C./ 4"C-I130Mep,
CH 3 .... eCJ1111 no pa3Hbie - "no
, U"c- ' CH
:3 TpaHc . 11130Mep.
28

CSOMCTsa anKeHOS
C 2 -C. ra3bl, 4,. CS-C'B )l(I1AKOCTI1,
C>19 TBepAble, p<1 rjcM S , Mana
paCTBOpl1Mbl B BOAe, T,"n(H»T,"n(pa3B.)
T,"n( lJ,I1C) > T,"n(TpaHC)
XIIIMIilLfeCKlile AKTIIIBHbl 1113-3a Hanlll'.IIIISI HenpO'lHOM
CBOMCTBa n-CBSl3111
cl>1II3l11LfecKlile
CBoVicTB8
XapaKTepHbI peaKlI,lI1I npIICOe,lJ,IIHeHIIH
CBOL-1CTBa
I. rOpeHl.1e
npl1Mepbl
C n H 2n + 3; 0 2  n CO 2 + n H 2 0 + Q
n=2
C 2 H. + 30 2  2C0 2 + 2H 2 0 + Q
II. PeaK1..\1.11.1 G + -
npl.1COeAIIIHeHIIISI : C  C: + H - X ---7
1)rlll,qplllpOBaHlile
(npL1COeAL1HeHL1e
BOAopoAa)
2) ranoreHlllpOBa-
Hille (npL1COeAL1He-
HL1e ralloreHOB)
06eCI.\BeL1BaHL1e
6pOMH0i1 BOAbl
3) OKlllcneHllle [Q]
(p-p KMnO, -
o6eCLlBe'fIilBaHllle)
I G I
-C - C- sp'->sp'
I I
H X
to
CH s -CH -+- CH 2 +H 2 -?CH s -CH -CH 2
I I NI I I
, , H H
(CH,-CH,-CH,) - nponaH
CH 3 -CH+CH 2 +Br 2CHs-CH -CH 2
I I I I
: : Br Br
"a'leCm6eHHaJt ( CH -CHBr-CH Br ) -
oe aJf ;!t- UR, 3 2
1,2-AL16pOMnponaH
CH 2 +CH 2 +[0] +H20CH2-CH2
J I
"a'leCm6eHHaJt OH OH
p ea,,  uJt 3TL111eHrnL1KOnb
3CH 2 =CH 2 +2KMnO. +4H 2 0=3CH 2 -CH 2 +2Mn0 2 +2KOH
I I
OH OH
29

I CBOMCTBa anKeHOB (npOAOmKeHlI1e) I
CBOL1CTBa npl1Mepbl
4) anKlllnlll- {CH 3 -CH,-CH,-CH,-CH 3
pOBaHlile CH,  CH, +CH 3 -CH 2 -CH 3 neHTaH
(np"coeA"He- CH -CH -CH-CH
Ht.1e aJlKaHOB) 32 1 3
kat AICI" AIBr" CH 3
HF,H,S04 2-MeT"1l6YTaH
5) rl/l,qporano- CH2  CH, +HBr --7CH 3 -CH,Br 6poM3TaH
reHlllpoBaHlile
(npt.1COeAt.1He- 1i+ 08- + - rCH3-CH,-CH,Br2
Ht.1e raJ10reHO-
BOAOPO,L\OB) CH3--7CHH, + HBr
- - - -; CH 3 -CHBr-CH 3
AllSi HeCIilMMeTplll'fHbIX - npaBlilno MapKOBHIIIKOBa
AmoJft BofJopofJa za..wzenoBofJopoiJoa u iJpyzux HeCU.!H..llempU'iHblX BofJopofhiblX COeOWleHUU
npucoeiJuH.flemCIl 1C Hau6aJlee zuiJpozeHu3upoBaHllOMY (60JlbLUe amO.1106 6otJopofJa) amo.lry
yutepo8a npu iJBOll1wil C6.1t:3U.
MexaUU3M uouub,ii CH 2 =CH,+HBr
H Br H
H : : H +:$/:- --7H: : : H+:--7H: : : H
H H H H H H
--------
8 I 8 I
UCKJl,70"IleUUe CH3  H2 + HcI--7 CH 3 -CHCI-CH 2 CI
t 1,2-A",xllopnponaH
CI
6) rlll,qpaTaLlIIISI
(npMCOe,l],IIIHeHLtle CH,  CH2+H,O -4 CH 3 -CH 2 OH
BOAbl) COrIlaCHO
npaBItlI1Y MapKOB- p, kat
HIIIKOBa 3T"llOBbJi'i Cnt.1pT
7) nonlilMeplll- r
3aLlIIISI n CH  CH'p --7 ( -CH-CH,- )n
I . kat I
e, p, CH 3 CH 3
ka1 AI(C,H 7 ), npOnt.111eH nOllt.1npOnt.111eH
30

CBOL1CTBO YpaBHeHL1e npL1MeHeHL1e
1. nOll"Mep"- nCH,=CH,( -CH 2 .CH 2 .)n npOlll3BOACTBO
nllaCTMacc
3alJ,lIIf1 nOnt13T!i!JleH
CH 2 =CH, +CH 3 -CH 2 -CH 3  B r<2yeCTSe
2. AnK"ll"'po- MOTOpHOro
BaHllle  CH3.CH2-CH2-CH2-CH3 TOnJll.1Ba
neHTaH
3. faIloreHIII-
posaHIII8 III CH,=CH 2 +CI 2  CH 2 CI-CH 2 CI PacTBoplIITenb.
rtIIAporano-
reHlllpOBa- AIIIXIlOP3TaH
H"e
MecTHaS'l aH€CT€3111f!,
CH,=CH 2 +HCI -4 CH 3 -CH 2 CI paCTBOpl/lTellb, B cjx
AnSi o6e33apa>KIIISaHIIIs:!
xllopsTaH SepHQXpaHi:1J1It1LLJ..
4. f"ApBTa- CH,=CH,+HOH -4 CH 3 -CH 2 OH PaCTBOplllT€llb, B
Mep,I/IlJ,IIIHe, B npollls-
I1"H ::miJ1l0Bblll1 cnlllpT Bop,CTse CMHT€TIIIY€C-
I(Oro KaY'-IYI<a.
5. OKII1CneHIII8 nOilYlJeHIt1€ 8HTIIICPPJ;1-
CH 2 = CH,+[O]+H,O-4 CH 2 -CH 2 30B, TOpM03HbiX >K!II,IJ.-
[0] p-pOM J I KOCT€IIi, B npOIli380JJ.CT-
KMnO, OH OH Be nl1aCTMacc.
6. Oco6ble OH npenapaT "sTpeIl"
CBoLllcTBa ' . I HO (1946r. M.L1.Ka6aYHMK
CICH -CH P=O  VI n.A.POCCII1t1cKafl)
aTIIIlleH8 . 2 2. nonap,aS'l B paCTeHVI€,
, , I
STlt1118H - OH pa3JlaraeTCS'l c
peryllHTOp Bblp,el1€HIII€M 3TI/IJl€Ha,
paCTa CH 2 =CH 2 + HCI + H 3 PO. YCKOpS'l€T COXpeSaHII1€
pacT8Hllltii nflO,lJ,OB.
npMMeHeHMe anKeHOB
31

nonY"IeHMe anKeHOB
1. 1113 CniolpTOB 
KaTall"'TI-1eCKa Aer"'ApaTal\l-1
nOPAOKF1TLlj1reHI-1 BOAbl onpeAeneTc npaBlilnoM 3a£lLleBa.
I I r
H-C-C-H - CH 2 :;;:;: CH 2 + H 2 O
I I H 2 SO 4
H- - -OH'
-----...
llpu iJezuiJpamaqull Cnltp1710B aoiJopoiJ omllenJl.flemCfl om 7iaUJvWHee
zuiJpozcHll3upoBaliHozo (.MCHblUC amO.MOB aoiJopoiJa) anw.Ma Y2JlepoiJa.
2. 1113 MOHOranO.-eHnpOIll3BOAHbIX -
Aerl-1JJporalloreH 1-1 pOBaH"'e.
CH 3 -CH 2 -Cl+KOH - CH 2 ::::: CH 2 +KCI+H 2 O
(CntlipTOBOi1 p-p)
3. 1113 ranOreHnp01ll3BOAHb1X.
r
CH 3 -CH-CH 2 +Zn(nblnb)- CH 3 -CH=CH 2 +ZnBr 2
I I
Br Br
4. 1113 npeAenbHblX - Aerl-1.Apl-1pOBaHl-1e.
r
CH 3 -CH 3 - CH 2 =CH 2 +H 2
Ni
5. KpeKIIIHr HeTenpOAYKTOB.
r
C 16 H 34 ____ C S H1S+C s H16
32

AMeHOBble yrneBoAOpOAbl
(anKaAMeHbl)
C n H 2n - 2
HenpeAeJ1bHble yrneBoAopOAbl,
COAep>Kaw,lt1e B yrnepoAHoil1 l\enlt1
MOJ1eKYJ1bl ABe ABOHble CBS131t1.
n>3
KnaCCIiIIiIKaL4I,'lS1 no nOnO>KeHIilIO ABOiiiHblX CBSl3eiii
CH,=C=CH,KYMYll"'POBaHHble CBHSI1 (HeYCTOi'iI1Bbl)
CH 2 =CH-CH=CH 2 conp'''KeHHb,e CB"3"
CH 2 =CH-CH,-CH=CH, I13011"'pOBaHHble CB<1311
CTpoeHllle (CBoi'icTBa allKeHOB B 2 CTB.L\I1"')
6YTa)J,l1eH - 1,3
1 2 3 4
CH,=CH-CH=CH,
Sp'r,,6p"',!\"'3aL\"'S1
max 311eKTpOHHaH
nllOTHOCTb Me>K,L\Y
1,2 " 3,4 aTOMaM"
yr llepo,!\a
CTpoeHllle MoneKYJlbl
6YT8AMeHa - 1,3

aH ----7 AllieH
CH,=C-CH=CH,
I
CH 3
2-MeT"n6YTa,L\"eH-1,3
("'30npeH)
HYMepaL\"'S1 C TOro KOHL\a, r,!\e 6n"'>Ke ,!\BOMH CBS13b.
LI,,,,<j)Pbl B KOHL\e YKa3blBalOT nOnO>KeH",e ,!\BOMHOM CBS13"'.
yrnepo,qHoro CKeneTa
CH =C-CH=CH
I GH,=CH-CH=CH-CH3 'I '
neHT8)J.(.1eH-l,3 CH g
2-MeTltUl6yraA!I!eH-l,3
H30MeplllSi .-.nonO>KeH"" ,qBOHHbIX (KpaTHblx) cBSl3eH
CH, =C=CH-CH, CH,=CH-CH=CH
\ 6YTap,lAeH-l,2 6yraA!I!eH-l.3
KnaCCOB coeA"HeHIIIH (allK"Hbl)
CH, =CH-CH=CH, CH"" C-CII ('11
6yr8.Al1eH-l,3 6YIL1II I
33
HOMeHKnaTypa
/\
1 2 3 4
CH,=CH-CH=CH,
6YTaA",eH - 1 ,3
(A"'BwHwn)

XMIiILfeCKe CBOCTBa anKaAlileHOB
(C COnpSl>KeHHbIM CBSl3S1M). nony...eHe
nOXO>KIII H3 anKeHbl, 60nee 3KTIIIBHbl. Ha6n1OAaeTC" B3aMMHOe
Bll"'''HMe ABOHblX cB"3ei'i, n03TOMY BC" HeHaCblLljeHHaH CMCTBMa
npM peal<l1"'HX np"'COeA"HeH"''' pearMpyeT KaK OAHO WellOe.
1. rtlApl(!poBaHf.1e
CH 2 + CH - CH + CH 2 + H 2 -7 CH 3 - CH = CH - CH s
I . I I
I I I J 6YTeH - 2
1-____ ,
2. tanoreHlllposaHlile -
{CHCH-CHCH "_.,
I 2 I 2 (MaIlO)
CH + CH - CH+CH +Br Br Br
I 2 1 I 2 2
I . I I
, 'n _ _ _,' CH 2 -CH=CH-CH 1,4-AM6pOM6YTeH-2
J I 2 (OCHOBHO
Br Br npOAYKT)
nplllcoe,qIllHeHllle l/I,qeT B nOnO>KeHllle 1 III 4, 3 Me>K,qY
3TOM3MIII 2 III 3 o6p33yeTcSl HOBaSi ,qBoHHaSi CBSl3b.
3. rlilAPoranOreHtlpOBaHlile
CH 2 = CH - CH = CH 2 + HCI-7 CH s - CH = CH - CH 2 CI
I I I I
I 1- _ __ I I 1 - xnop6'YTeH - 2
4. nonlilMeplll3aLltlSl
c; Kat
CH 2 = CH - H = CH 2 -7 (-CH 2 - CH = CH - CH 2 -)n
I i I I no.nL16YTaAlI1eH
I I I
1- _ __ (6YTaAllleHOBblill KaY'-IYK)
nonY"IeHllle:
1. Kamflll1TII1'1eCKOe ,lJ,erll1,lJ,pll1pOBaHlI1e aflKaHoB(a), aflKeHoB(6).
a) CH,-CH 2 -CH 2 -CH, CrO,/AIO. CH 2 =CH-CH=CH,+2H 2
" )
700'C
6YTap,eH - 1,3
6) CH 2 =CH-CH,-CH s ,. CH 2 =CH-CH=CH 2 +H 2
Kat)
2. no cnoco6y fle6e,lJ,eBa.
2C,H s OH 400' -500' S CH 2 =CH-CH=CH 2 +2H 2 O+H,
Kat.
34

06lL!,aSl XapaKTepCn1Ka KaY"'YKOB.
I>1x CTpOeHe  CBOCTBa
KaY'fYKIII-3naCTOMepbl - BblCOKoMolleKynflpHble Bell\eCTBa,
COXpaHfllOll\",e CBOIO 3naCTMHOCTb B W"'POKOM "'HTepBalle
TeMnepaTYP. nerKO M3MeHflIOT q,OPMY np'" BHeWHeM B03AeL>icTBM"',
nocne OKOHaHMfI B03AeL>iCTBMfI npMH"'MaIOT MCXOAHYIO.
HaTYpanbHblH KaY'fYK - npMpoAHblL>i BbICOKoMolleKynflpHblL>i, He-
npeAellbHblL>i yrneBoAopOA (C,H 8 )" n= 1000-3000 ( -CH, -C=CH-CH' 1
MneHbli'i cOKAepeBa reBe",. H,O, CO"hV(CBeT)--> tH, n
.'lCao-.."y" - Cne3bf, iJepe6a - ocmpo6 raumu l13GnpeH
(nam. AJlwpUJ,a) - Xpucmopop IConYJtL6
Ba>KHeHWllle CBoHcTBa: 311aCT"'HOCTb, M3HOCOYCTOL>i"'BOCTb,
BOAO- M ra30HenpoH"'l\aeMOCTb, XOPOWML>i "'3011fITOp, pacTBopfl-
eTCfI B opraH"'eCKMX paCTBOp"'TenfiX.
He,qOCTaTKIII: np'" BbICOKOL>i e - pa3MHraeTCfI,
nn", HM3KOL>i e -xpvnK"'i'i.
CIIIHTeTIII'feCKIIIH KaY'fYK (1932 r. C.B. ne6eAeB r. 51pocllaBllb)
6 - No ( -CH" / CH'- j
CK,IJ, YTa,L\MeHOBbIM n CH,=CH-CH=CH,  / C=C \
'H H
C 6 ,H,OH ); 6YTMlleH --> 6YTBAMeH --> CKjJ, U"C
YTBH
CBoi'icTBa: BOAO- M ra30HepOHMl1aeMOCTb, YCTynaeT no 311aCT"'1-
HOCT'" M M3HOCOCTOL>iKOCT"'.
CK'" M30npeHoBbli'i (l\MC-"'30Mep) cTepeoperYllHpHoro cTpoeH"'H
,. ( CH,C=C H )

-CH, CH,- n
n CH,=C-CH=CH,
I
CH,
neHTaH --> MsoneHTaH --> "'30npeH --> CK\I1
np"'poAHblL>i KaYK - TOT >Ke COCTaB.
s
BynKaH"3aLlIIISl: KaYYK  pe3"Ha (6011bwa 311aCTMHOCTb,
npOHOCTb, YCTOi'iMBOCTb K Aei'iCTBMIO 1° '" paCTBOp"'TelleL>i).
... -CH, -CH=CH-CH-...
I
Sx
I
.. -CH,-CH,-CH-CH,-...
npOIl1CXOAIIIT nonepeLlHoe CWIIIBaHlt1e MoneKyn
Me>K)J,Y co6oiii AIIICYJlbcplllAHblMII1 MOCTIIIKaMII1.
06pasyeTcH npocTpaHcTBeHHa ceTKa. ECJl
cepbl MHoro - 360HlIIT (OTJlIl1LJHbI1l111130JlflTOp).
...-CH,-CH=CH-CH,-...+xS 
x OT 1 AD 4
35

. AeTIIIJ1eH (3TIIIH). CTpOeHllle
MoneKynbl. Sp rIll6pJ.1AIII3aIIISI
C H I, , \ p B BOAe T KMn .= - 83,8°C
2 2 ATOMbl yrnep o J3a B MoneKyne al\en1neHa
o6pa3YJOT TpOMHYIO CBSJ3b, HaxOASJTCSJ B
COCTOSJHL1L1 sp rIt16pIt1AIt13al\lt1lt1.
Mr=26
2S 1 2p3
c*

S
1 S + 1 P --? 2SP
180"
Ase SP
Op6MTanM
MoneKyna m1t1eMHa,HerM6pMAHble 06naKa 06pa-
3YIOT ABe 11: CBSl3M BO B3aMMHO .1 nnoCKOcTSlX.
A{C""C} COCTaBnfleT 0,120 HM
!
, "
J, I"
C5
H-c n C-H
n
Q -
, -.
'.
 .t.....  -.....
+ ., : . . .:; --? . . .
':,...
S
Px

CpaBHeHllle CTpOeHIIISI MoneKyn 3TaHa , 3TlllneHa
III aLl.eTlilneHa. CpaBHeHllle a-III n-CBSl3eiii
npMSHaK'" cpaBHeH"fI 3TaH 3T",neH AL\eT",neH
1.8",[\ r,,6p",[\"aa"" sp' sp' sp
2.BHAbl CBSl3" a-CBflSb a-, n-CBflSb a-, ABe
yrnepoA-yrllepoA n-CBs:!3111
3.A11"Ha CB"a" 1c(HM)
(paccTOflHlI1e Me>KJl,Y 0,154HM 0,134 HM 0,120 HM
4eHrpaMIt1 aTOMOB
yrnepoAa)
4.npO'fHOCTb CB"a" 350 620 810
(sHepr"H) K)],)I(/MOllb KA>K/MOllb K,!J,)I(/MOllb
5.CTpoeH"e TeTpa- nllOCKoe I1[11HeI:1HOe
3APMecKoe
npM3HaK'" cpaBHeHMfI a( Cl1rMa)-CBfl3b n(nl1)-CBfl3b
06pa30Bamfe CBR3H
1.BM,[\ nepeKpblBaHMfI OceBoe nepeKpblB8Hllle 50KOBoe nepeKpblBa-
slleKfpoHHblX (CBSl3111 HaXOA51TCSl Ha Hille (CBSl31t1 BHe rlnoc-
0611aKOB npSlMO, coeAIt1HSlei1 KOCT" a-CBHS"', -1-)
u,eHTpbl aTOMOS)
2.CTeneHb 3HaLJIt1TeI1bHafl He6011bwaH
nepeKpbIBaH"'
3. YaCTBYIOT r,,6p"AHble Her,,6p"AHble
3JleKTpOHHbie 06naKa 3JleKTpOHHbie 06naKa
4.nOllO>KeH"'e CBHS'" CBH3b HaxoA"TCfI B CBHSb nepneH,q"KY-
nnOCKOCTIil Mone- nSipHa nllOCKOCTM
KYnbl O-CBfl3M
Oco6eHHoCTH CBR3H
1.np04HOcTb CBHS'" BbICOKaSl- He6onbwaSl-
(sHepr"'H CB51S"') 350 K)J,>K/MOllb 270 K)J,>K/MOllb
2.nOllHpMSaI1M CBS'" cna60 nerKO
nOllHpL-13yeTcH nOll51p"'syeTcH
3.Cnoc06HoCTb Bpa- cB06o,qHoe OTCYTCTByeT
Ll1eHM aTOMOB BpaLl1eH"'e cB060AHoe
BOKpyr CBH3M BpaLl1eHMe
4.Cnoc06HOCTb K XM- HM3KaSi BblCOKaSi
MMeCK"'M peaKL\MHM
37

AnKIiIHbl (aeTliineHOBble
yrneBoAOpOAbl)
C n H 2n . 2
HenpeAeJlbHble ymeBoAopOAbl, B
MOJleKYJle KOTOpblX I1MeeTCSl OAHa
TpOHHaSi CBSl3b Me>K,D,y aTOMaMI1
ymepOAa.
A /'-.
HOMeHKJlaTypa aH --7 IiIH
Bbl60p rnaBHoVi lJ,en\i1 \i1 Ha4ano HYMepalJ,\i1\i1
onpeAenS1eTcS1 TPOVlHOVI CBS13blO.
5 4 S 2 1
CH s -CH-C - C-CH 3
I
CH 3
4-MeT\i1nneHT\i1H-2
yrnepoAHoro CKeneTa C "c" 5
I CH:=C-CH2-CH2-CH3 CH = C- y H-CH 3
neHT"H-1 CH 3
3-MeTIIIIl6yn1H-1
1A30MepIllSl-nOnO>KeH....e TpOi1HOi1 (KpaTHoi1) CBSl3....
\ \.. CH = C - CH 2 - CH 3 CH 3 - C = C - CH 3
 6yn1H-1 6yr1llH-2
KnaCCOB coeA....HeH....i1 (anKa,D,l-1eHbl)
CH == C-CH 2 -CH 3 CH 2 =CH-CH=CH 2
6ynilH-1 6yra)J,lIIeH-1,3
 npocTpaHcTBeHHoi1 HeT
(J)1II3111"1eCKlile CBoCTBa
C 2 -C 4 ra3bl,C s -C 16 )l(I1AKOCTI1, C?17 TBepAble Bell\ecTBa,
paCTBOpl1MOCTb B H 2 0 He6oJlbWafl,HO 60JlbWe 4eM y
aJlKeHOB 11 aJlKaHOB, p < 1 r/CM 3 ,T'K"n(H»T'K"n(pa3B),
C YBeJll14eHI1eM Mr T'K"n YBeJlI14I1BaeTCfI.
38

XIIIMW.leCKllle CBOMCTBa anKIllHOB
I. rOpeHe (MHOro C,nnaMS1 KOnTS1ll\ee,
npl1 BAYBaHl111 O 2 CBeTI1TCS1,r=2500"C).
2C 2 H 2 + 50 2 = 4C0 2 + 2H 2 0 + Q
II. PeaKLI npCOeAHeHSI
"- / "- /
-C=:=C- --7 C=C --7 -C-C-
/ "- / "-
Sp Sp2 Sp3
1) rHJ1,pHpOSaHHe
CH=:o CH + H2( CH 2 = CH 2 Ni
CH =:0 CH + 2H2(Pt) CH 3 - CH
2) ranoreHHposaHHe (c 6pOMHOM B0,l10M -06eCLjBe£1BaH£1e)
Ka'feCTSeHHaSl p ea KLl VlSl
CH=:=CH+Br 2 --7 CH=CH CH = CH + Br --7 Br-CH-CH-Br
I I I I 2 I I
Br Br Br Br Br Br
1,2-A"6pOMSTeH 1,1,2,2-TBTpa6pOM3TaH
3) rHJ1,pOranOreHHposaHHe (npaB/I1flO MapKOBH/I1KOBa)
CH=:oCH+HCI--7 CH 2 =CHCI
EJIIIHlllnxnoplllJJ.
4) rHJ1,paTaLlHSI kat HgS0 4 ( Hg(N0 3 )2)
PeaKLj/l1f/ KYLJepOBa
. Hg+ O
CH=:oCH+H 2 0;tsct CH 2 =CH-OH --7 CH 3 - C 'H
BIIIHl''lnOBblij cnlllpT YKCYCHb! anbAf;rll1J],
CH 3 - C =:0 CH + H 2 O--7 [CH 3 - C = CH 2 ] --7 CH 3 - C - CH 3
I "
OH 0
au,eTOH
39

I
XIIIMW"leCKllle cBoiiicTBa anKIllHOB
(npO,lJ,OJDKeHlIIe)
III. OKIo1CneHl-1e -nerKO [0]
(p-p KMnO.-o68CLJ,B81.1!/1BaHI.18)
Ka.,eCTBeHHaR o eaK U HR
CH - CH +[0]+ H 2 0  HOOC - COOH
ll\aSenesaS1 KHcnOTa
IV. Tpl-1Mepl-13aLl.Io1S1 (AIlS! aLJ,8TI.1Jl8Ha)
3CH = CH C T ) C 6 H 6 ( 0 )
68H30n V
V. 3aMeeHlo1e BOAOpOAa y aTOMa
yrnepoAa C TPOV!HOM CBSl3blO
2CH = C - CH 3 + Ag202AgC - C - CHJ + H 2 0
(aMM"'aHblC1
pacTBop)
CH - CH + 2Na CNa = CNa + H 2
all,eTHneH"'A Na
40

nplllMeHeHllle aeTMneHa
CBOL>iCTBO YpaBHeHf1e np"'MeHeH",e
1. rOpe- 2C,H, +50,-74CO,+2H,O+Q ABTOreHHaS1
Hl1e CBapKa '" pe3-
to fJ,O 3000°C Ka MeTaJlnOB
2. rallore- PacTBop"'Ten""
Hl1pO- CH == CH + 2CI 2 ---7 nonyyeH",e
BaHl1e ---7 CHCI 2 - CHCI 2 APyr",x
npO"'3BOAHbIX
3. rl1fJ,pO- CH '" CH + HCI CH,= CHCI ,QnS1 npO"'3BOA-
rallore- XnOpBIIJHllln CTBa non",-
HMpO- B"'H",nxllop"'Aa
BaHMe nCH, = CHCI  (-CH'-yH-) (KO>K3aMe-
CI n H"'Tenb '" T.n.)
","0 nonY'feH"'e YK-
4. rl1fJ,pa- CYCHoro anbAe-
TaL.\l1f1 CH '" CH + H,O-> CH 3 -C rf1Aa, YKCYCHoL>i
'H K",cnOTbl
(->naKf1, neKap-
CTBa MAp.)
,+
5.3aMe- CH '" CH + 2Cu -> CuC '" CCu..!. A'-\eT",neHMAbl
aMMlI1aLJHblW
ll.\eHMe - B3pblB'faTble
p-p BeU.\eCTBa
CH",CH + 2AgN0 3 +2NH 4 OH->
-> AgC",CAg..!. +2NH 4 N0 3 +2H,O
nOClle BbICYW"BaHf1H - BB
4 3ali. 58
41
.

nonY"IeHllle a....eTlllneHa III ero
rOMonorOB
1. AerMAPMpoBaHMe anKaHOB
Ni
CH 3 - CHs"f 2H 2 + CH = CH
2. 1f13 npMpoAHoro ra3a
2CH4  3H 2 + CH = CH
3. l(ap6MAHblM cnoco6
CaC 2 + 2H 2 0 --7 Ca(OH)2 + CH - CH
4. 1f13 AMranoreHnpoM3BoAHblX -
-AerMAPoranoreHMpoBaHMe
CH 3 -CHCI-CH2CI+2KOHCH3 -C = CH+2KCI+2H 2 O
(cnll1pTOBblM
paCTBOp)
111m"
CH 3 -CCI 2 -CH 3 +KOH  CH 3 -C = CH+2KCI+2H 2 O
( cnlllpTOBbllii
paCTBOp)
42

6eH30n. 4>1II3W-IeCKllle CBOMCTBa.
4>opMyna KeKYne
C H OTKpblT M.CPapaAeeM B CBeTll1JlbHOM ra3e 1825 r.
. >KI1AKOCTb, },j", 3 xapaKTepHblH,
6 6 T"n =80"C, Tnn =5,5"C, He paCTBOpl1M B H 2 0,
.p <1 rjcM 3 , XOPOWMH paCTBOpl1TeJlb, SlAOBIiIT
npOTl-1BOpe'lll1e: 6eH30Jl - CI1JlbHO HeHaCbllL\eHHblH
yrJleBOAOpoA, HO YCToC1'-1I1B K AeHcTBl110 OKI1CJlIrneneH,
He 06eCl(Be'-lI1BaeT pop KMnO. 11 Sr 2 BOAY.
BbIXO/1,: CTpOeHl1e 6eH30na


27 flHBapfi 1865 r. - 'AeHb pO>K,£!eHMfI"
mopMM cTpoeHMfI 6eH30na,K3K apoMaTM-
.,eCKoro coeAMHeHMfI - AeHb,KorA3 6blfla
ony6nMKoBaHa B ElOnnemHe napM>KCKoro
XMMM.,eCKoro o6lljecTBa MHcJ;OpM3/{Mfi 0
"KOHCTPYK/{MM apOMaTM.,ecKMx BelljeCTB".
, ,<'
,QOKa3aTenbCTBO 4111KJ1Ii1'JeCKoro CTpoeHIiIR 6eH30na
1. CI<1HTe3 1<13 al1eTI<111eHa (1866 r. 6epTllo)
3C 2 H 2 t' ;;'O'C) C 6 H 6
2. fl<1APl<1pOBaHl<1e 6eH3011a --> I1I<1KllOreKcaH (npl<1COeAI<1HfleT
TOllbKO 3H,) --> AOKa3blBaeT 111<1KJ1"'HOCTb 1<1 HenpeAellbHOCTb
CH,H=CH,
+3H 2 ,NI,150"C
Ca6an,e 1900 r.
I
H
I
C
H-C O ' I C-H
H-C " C-H
C
I
H
t
- , Ii-
... H' H
,  /
, ' O /C /H
\.. C'll"'....,
H/ I HI
H }H,
,_ C,'J
,H 'r H
, ' <,
" H" H
3en1l1HcKiIIC11912 r. - 'J I
-3H" Pt,300'C
4'
43

3neKTpOHHoe CTpOeHe 6eH30na I
npOTVIBOpe'l/l1e: no cJ>OPMyne KeKYne B MoneKYne C.H.
- Tplil ABOMHble CBSl31i1, HO 6eH30n He 06eC4Be'lIilBaeT
p-p KMnO. iii Sr. BOAY.
Pa3BI1TI1e KBaHToBoi-i MeXaHI1KIr1 AOKa3ano, '-no B Mone-
Kyne 6eH30na HeT OAI1HapHblX (C-C) 11 ABOi-iHbIX (C=C)
CBfl3ek Bce yrnepoA-yrnepoA CBfl311 paBH04eHHbI,
AJlI1Hbl cBfl3ei-i paBHbl. CYlL\eCTByeT OC06blM BI1A CBfl311
- KpyroBoe n-COnpSl>KeHlile

C
H- c 0 C - H I1nl1 0
H-CVC-H V
C
I
H
MOfleKYflB nflOCKBfl, BTOMbl
"C" 06be/l,II/HeHbl B npB-
BlI/flbHbliit WeCTlI/yroflbHbliit
4/11Kfl, HaxO/l,flTCfl B COCTO-
flH1I/1I/ Sp2 r1l/6plI//l,1I/3B411/11/
BBfleHTHbliit L120"
A c _ c = 0,14 HM
WeCTb HecnapeHHblx Herl16pl1AHbiX p-3neKTpOHOB o6pa-
3YlOT eAI1HYIO n-3neKTpoHHYIO cI1cTeMY (apoMaTw'JecKoe
flAPO) , KOTopoe pacnonaraeTcfI nepneHAI1KynflpHo K
nnOCKOCTI1 6eH30nbHoro Kon, bl.\a nepeKpblBaficb APyr C
APyroM cBepxy 11 CHI13Y 3TOi-i nnOCKOCTI1.
H
""0
H H
CxeM8 06pa30B8HVlfI
O-CBs:l3e B MoneKyne
6eH30na
CxeMa 06pa30B8HVl5I 1t-3J1eKTpOHHOW
CIt1CT€Mbl B MoneKYJle 6eH30na
44

XIIIMIII"IeCKe CBOVlCTBa 6eH30na I
I. rOpeHllle - Cl1nbHO KOnnHl.\ee nnaMfJ
(HecropeBWl1e LJaCTIr1LJ,bl C).
2C 6 H 6 + 150 2 == 12C0 2 + 6H 2 0
CXO .n CTBO C n p e .n enbHbIM.....
II. YCTOit"llllB K AeitcTB1ll1O oKIIICnlllTeneit
npl1 06blLJHbiX ycnoBI1S1X He 06eCLJ,BeLJI1BaeT p-p KMn0 4
(nepMaHraHaTa Kanl1S1) 11 Br 2 BOAY.
\II. PeaK41i1111 3aMew.eHIiISI (3neKTpocpl1nbHoe)
KaTanl13aTOp nonfJpl13yeT MoneKyny
o
O H
 X" 
+X+-7  I -7(YX
-7 Ox + H+
1t- KOMnI1eKC (j- KOMnl1eKC
1. HvITpOBaHVle (cMecb HNO,(K) VI H 2 SO.(K))
o
+ Ho:IN0 2
8aOTH3S1
KI<1CIlOT3
H 2 S0 4

ONO,+ H 2 0
HI / 1Tpo6eH30Il
2. ranoreHVlpoBaHVle t" ,kat FeCI 3 (FeBr 3 ),AICI 3
o + Br 2  OBr + HBr
6pOM6eH30I1
45

XIllMw..eCKr.1e CBOVlCTBa 6eH30na
(npOAOn>KeHHe)
3. AnKlllnlllpoBaHt1e kat AICI 3 (o6pa30BaHllle IOMonolOB)
a) ranoreHonpolll3BO/l,HblM anKaHa
C;, o t" 0 0 C,H,
+C2H5CI AICI?  +HCI
aH1J16eH3011
6) onecplI/HOM
CH CH
HC @ C;   HC @ C-C'H'
: - t" 0
o ":.+CH 2 -CH 2 AICI? HC CH
HC c CH
CH
CxonCTBO C HenpenenbHblMM
IV. PeaK4HH npHcoeAHHeHHSI C TPYAOM, T.K.
npOI1CXOAIr1T pa3pyweHI1e YCToC1'-1I1BOCi
apOMaTI1'-1eCKOCi CI1CTeMbl
1. IIII/l,plllpoBaHllle
o +3H 2 O
LU.1KnoreKC8H
2. laflOreHlllpOBaHllle (hV-cBeT,kat)
Cl g H CI H
H CI
CJ H
H CI
CI H
reKcaxnOpKJlOreKcaH
(reKCaXJlOpaH)
B omuuu OT Henpe/1eflbHblx + H,O, +HHal, +p-p KMnO, 
o
+ 3C12
' no XHMHLleCK"'M CBoHCTBaM 6eH30n 3aHHMaeT ,
KaK 6bl npOMe>KYTOLlHoe nOnO>KeHHe Me>KAY
. npeAEmbHblMH H HenpeAenbHblMH yrneBoAOpo-
AaMH (oco6oe :,meKTpoHHoe CTpOeHlAe) ·
46

ApeHbl (ApOMaTeCKe
y...neBOAOpOAbl.AnKn6eH30nbl)
C n H 2n . 6
COeAI1HeHI1Il, MOJleKYJlbl KOTOpblX COAep)l(aT
.YCTOM'il1Bble l\l1KJll1'ieCKl1e CTpYKTypbl - 6eH-
30JlbHbie IlApa , C OC06blM XapaKTepOM CBIl-
3eiii. (I1CTOpl1'ieCKl1 "apOMaTl1'ieCKl1e"- I1Me-
1OlL\l1e npl1llTHbliii 3anaX)
c:;;,6
HOMeHKl1aTypa Ha3BaHI1e 3aMeCTI1TeJlll + 6eH3011
(aJlKI1Jl)
HYMepal\111O HaLJI1HaTb C OAHOro 113 aTOMOB yrJlepOAa,
npl1 KOTOpOM eCTb 3aMeCTI1TeJlb. XapaKTepHbl TpI1BI1-
aJlbHble Ha3BaHI11l (TOJlYOJl, KCI1JlOJl, KYMOJl)
PaAI1KaJl apOMaTI1LJeCKI1X
yrJleBOAOpoAOB - aplill1
C6HS- I1JlI1
0-
@
e".
<jJeH"ll
Men1Jl6eH3011 1,3 -AItIMeTVlJl6eH30Il
(TOllYOll) (MeTB-KC"llOll).
a3MeCTlilTeneH
/ C0- 0 CH,-CH,-CH,
M30MeplilSi 
 PonIt1Jl6eH30Il
(<jJeH"llnpOIlBH)
He rOMOJlOrl1
 n0110>KeHIIISI a3MeCTlilTeneH
 CH, CH,
 o Ha<jJTan"H o 0-CH,
  @te.
aHTpau,eH
CCH,
 '-CH,
1t130npon1l1I16eH3011
(<jJeH"ll"sonponaH)

CH,
.2 -AIIIMen1J16eH3011 1.3 -AI.1MeTI1116eH30fl1,4 -AIt1MeTIiIJl6eH301l
(OpTO-KC!t11l01l) (MeTa-KCIt1J10n) (napa-KCIIII101l)
47

Tonyon.XHMHeCKllle CBOVlCTBa.
BaaHMHOe Bn.....HH.....e aTOMOB
B MoneKyne Tonyona
CH 3 rOMOJlOr 6eH30Jla. OAj,1H 113 aTOMOB BOAopOAa
@ B 6eH30JlbHOM KOnbl.\e 3aMell.\eH Ha paAI1Kan -
O MeTI1Jl (C 6 H 5 -CH 3 ).
rOMOJlOr MeTaHa, B MoneKyne KOTopor aTOM
BOAOpOp,a 3aMell.\eH Ha apOMaTWJeCKI1j,1
Mem1l6eHsoll paAI1Kan - cpeHl1n (CH 3 -C 6 H 5 ).
BnHSlHHe MeTHnbHOH rpynnbl
CH, nepepacnpeA611eH"'e
0-£ 0- . 311eKTpOHHoi:1 nllOTHOCT'"
 B nOllO>KeHWe 2, 4, 6
0-
PeaKquu 3aMeUjeHuR uJJyr nerO/e, O/eM y 6eH30na
(Hal, HON0 2 , R-CI, CH 2 = CH 2 )
@ +3HON0 2 !3 NONO'+3H20
2.4,6 - Tp!:1HIIJTpOTOllyO.n
N0 2 (TOIl, TpOT!tm)
CH,
 BrBr + 3HBr
Br 2,4,6 - Tp",6pOMTOllYOll
BnHSlHHe 6eH30nbHOrO KOnbl..ta
AeticTBl1e nogKwcneHHOro paCTBOpa KMn0 4 npw HarpeBaHWM -
06eCl\BeMBaHl1e, rpynna CH 3 - nOABepraeTCfJ OKl1CJl8HMIO.
@--H+[Oh 1 @-l @-<:H+H,o
H l OH J 6eHsoHaH ""cnOTe
XapaKTepHbl J.1 APyrllle CBOMCTBa 6eH30na.
48
CH,
@ +3Br2

npaBna . OpeHTau.1II
B 6eH30nbHOM Konbu.e
OCHOBaHbl Ha B3al1MHOM Bnl1f1HI1I1 aTOMOB B MoneKyne
MeCTO BCTynneHIIISI HOBOrO 33MeCTlilTenSi onpe,qenSleTCSI nplll-
PO,qOj;! Y>Ke IIIMelOl1\erOCSI B 3pOM3TIII'feCKOM SI,qpe 3aMeCTlIITenSi
3aMeCTioITem.1 nepBOrO pOAa
rpynnbl aTOMOB, cnoco6Hbl8 OTAaBaTb S1l8KTpOHbi
(S1l8npOHOAOHopHble)
-R (-CH 3 , -C 2 H 5 , Lt1 T.n.),-OH,-NH 2 ,-Hal
OHI1 Opl1eHTl1pYIOT HOBbl1ii 3aMeCTI1Tenb B OpTO- 11
napa- nOnO)l(eHl1e (2,4,6)
06ner..,alOT peaKHH 3aMeLI.4eHHSI.
3aMeCTioITenill BToporo pOAa
aTOMHbl8 rpynnl<1pOBKI<1, cnoco6Hbl8 OTH1rI<1BaTb S1l8KTpOHbi
OT 6eH30JlbHOrO Apa (S1l8KTpoHoaKI1 8nTO pHble)
"",0 "",0 "",0
-N0 2 , -S03 H , -C'H' -C'OH' -C'R
OHI1 opI1eHTl1pYIOT HOBbl1ii 3aMeCTI1TeJlb B MeTa-nOJlO)l(eHl<1e
PeaKHH 3aMeLI.4eHHSI H.tIYT TPY.tI Hee .
NO N02MeTa-AHTpo6eH30
C NO @ ' @l (93%)
o_ @ H'O_O+ @ 'OrO+HONO' .) 0 + H 2 0
V 0 N0 2
CH 3 CH! OpTO-HVlTpoTonyon
0- Or @ H' @J
np"'CYTcTB"'8 saM8CT"TellH 0 +HONO,  0 NO, H
Ha pY UJa8T P aSM8Ll1€H"'8   c ,
napa-HIIITpo-
S1l8KTpOHOB B 68HSOllbHOM TOllYOll (40%)
Konbue. ()
NO,
(56%)
49

npMMeHeHMe 6eH30na.
nOnY"IeHMe apeHOB
n
p
111
M
E
H
E
H
111
E
HI-1Tpo6eH30Jl  aHIr1JlIr1H KpaCIr1TeJlIr1
C.H 5 NO, C.H 5 NH,
paCTBOplr1TeJlb
Ao6aBKa K MOTOPHOMY TOnJlIr1BY
6eH30Jl
C 6 H 6
---7XnOp6eH30Jl 
C.H 5 CI
1
<!JeHOJl<!JopMallb-
Aerlr1AHafi
CMOJla
<!JeHOJl j
e,",o"l
KanpOH
npOTpaBIr1TeJlb
ceMflH B c/x
C.CI.
1. BblAeJleHl1e 113 npl1pOAHblX I1CTO'-lHI1KOB (HeqHI1,
n KaMeHHoro yrJlfl)
o
n
y
LJ
E
H
111
E
AYWIr1CTble
SeLl\eCTBa
2. ApOMaTI13al.\l1f1 HeqHI1:
a) Aerlr1Apl1pOBaHl1e
l\I1Knonapa<j)I1HoB
6) l\I1KJlI13al.\l1f1 11
Aerl1APl1pOBaHl1e
aJlKaHOB
CH 2
H,C O CH, PI @
3H,+
H 2 C CH 2
CH,
CH 3 -(CH,),-CH, c;p') @ +4H,
3. TpI1MepI13al\l1f1
aJlKI1HOB
3C,H, :n) CoHo
4. AnKI1Jll1pOBaHl1e
6eH30Jla
O+C,H,CI AICI,) 0 C ,H'+HC'
npon"'1l6eHSOll
50

r CTpOn. HaTanH.AHTpaeH
)I(I1AKOCTb, 3 npI1SHHblC1,
M paCTBOpMM B H 2 0, T"",,= 145"
0  I CH=CH2
nOl1y"leHllte:
NCH,-CH, NCHCH,
V V +H 2
CHCH, \ -CH-CH'- ] 6elloe TBepAOe BeLl1eCT-
O 0 BO. np'" nOll"Mep"'3al\l'1'"
n 1f? I  1f? I B YCJ1OB"'X ':.cneH"'BaH"'
  peaKI1",oHHO'" MaCCbl -
n neHononlllcTpon
nplltMeHeHllte: non"cTpOll (neHonnacT)
3JleKTpOM30JlfJL\I1oHHbie MaTepMaJlbl, 6blTOBafJ nJlaCTMaCca,
AeKOpaTMBHblw MaTepMaJl, TenJlO- 11 3BYKOM30JlfJTOP
BVlHllln6eH30n
CT"POll

VV
HaqnalltllH
C1O H ,
(ABYXfJAepHafJ
apoMaT"'eCKBfJ
c",cTeMa)
aHTPal1eH
C,.H1O
(TpexHAepHafJ
apoMan1eCKafJ
CI<1CTeMa)
KpI<1CTallll"eCKoe BeLl1eCTBO, If. 3 xapaKTepHblL1,
M paCTBOp"M B H,O, T,,"= 80,3'C,T",,= 217,TC
nonY'feHllle: M3 KaMeHHoyroJlbHOC1 CMOJlbl
I<1JlM npOAYKTOB nepepa60TKM HecpTI1
nplilMeHeHllle: B np0l<13BOACTBe opraHI<1-
'1eCKI<1X Bell1eCTB, KpaCMTeJleW, neKapCTB,
KaK CpeACTBO 60pb6bl C BpeAHblMM
HaceKOMblMI<1
nO XIIIMIII'feCKIilM CBOHCTBaM cxo,qeH C
6eH30nOM
Kplt1CTanlllt1LJ8CKOe Bew,eCTBO, >KellTOe c rOJlY-
60L1 <jJlllOopeCl1eHl\I'1ei'i, He paCTBOp"M B H,O,
P B opraH"'eCK"'X paCTBOp"'TellHX,
T,," 216'C, T,,,,,= 342'C
nonY'feHHe: 113 KaMeHHoyroJlbHOW
CMOJlbl
npHMeHeHHe: B npOM3BOACTBe
KpaCMTeJleC1
nO XHMH'feCKHM CBoi1cTBaM CXOAeH C
6eH30nOM
51

reHeTIII"IeCKaSi CBSl3b Me>KAY
rpynl1aMIll yrneBoAOpOAOB
npeAel1bHble
C n H21l+2
MC BMC
, ,
AlIIeHOBbie H -
C"H 2 "_2 e
n
.t i p
3TI1neHOBbie e l\lIIKnOnapacjJlIIHbl
<-A
C"H 2 " e C"H 2 "
l' 1 11
b
al\eTl1neHOBble H
C"H 2 "_2 E- bl
e
'.

BMC apOMaTIII'feCKlile
C"H 2 " 6
J T
apOMaTI14eCKI1e
HenpeAenbHble ---? BMC
C I1 H 2n _ a
B
11 +2H
C n H 2n + 2 -2H 
11
-8H
1
-4H
11 +2H I
C n H 2n -2H) C n H 2n _ 2  C n H 2n _ 6 -=2j:( C n H 2n _ 8
i 1+6H
C n H 2n
+2H
52

06w,Me CBeAeHMSI
o rpynnax yrneBoAOpOAOB
3:' npe.o,BJ1bHble u.i<nona 3TL-1J1€HOBble aU€TtillleHO- apOMan1-
(aIlK8Hbl) paI.1HbI (aIlK€Hbl) Bble '-I€CKIt1€
Xapal<Tepa.1CTa.1K (aJlKIIIHbl) (apeHb')
06Ll1aS1 C n H 2n + 2 C n H 2n C n H 2n C n H 2n _ 2 C n H 2n _ 6
cjJOpMYlla
H
H H H H H H 1 H
1 "- / \ fl... I
H-C- H ' / C=C cOc
nepBbli:1 C H-C",C-H I I
H H / \ H / "- /C'c/ C ,
roMollor ....C-C.... H H
H'" ....H H H
,
H
MeTaH 1I,lr1KJ10npOnaH aTltm€H all,eTltlneH 6eH30J1
BalleHTHOCTb I I I I I
aTOMa -c- -c- -c- -c- -c-
ymepoAa I I I 1 I
B"'A
r",6p"'A"'- SP3 SPS SP2 SP SP2
3al1"''''
B"'A 0 c - c 0 c - c 0 c - c 0 c _ c 0 c - c
KOBalleHTHoi'i 0 C - H 0 C - H 0 C - H 0 C - H 0 C _ H
CBSl3111
1I: c _ c 211: c _ c 611-
-3J1BKTpOHHOe
COnp>KeHl-le
Yroll B 3aB"'C"'-
Me>K.L\Y 1 09 0 28" MOcrl/! 120 0 180 0 120 0
CB3M'" OT I1"'Klla
All"'Ha
CBm", c-c, 0,154 0,154 0,134 0,120 0,140
HM
53

061J..!.Me CBeAeHMSI 0 rpynnax
yrneBoAOpOAOB (npOAOn)l(eHl1e)
Sbl npe.o,€J1bHbl€ ltlt1KJ10na- an1J1€HOBbl€ alten11l€HO- apOMaTIr1-
(aIlKaHbl) pac1Jt.1Hbl (allK€Hbl) Bble Y€CKIII€
xapaKTepl>\Cn1K (aJlKIIIHbl) (apeHbl)
1.yrllepoA- 1. nOllO>Ke- 1.ymepOA- 1.ymepoA- 1. nollO>Ke-
Horo Hl!lfJ 3aM€- Haro CK8- Haro CK€- H"'H 3aMe-
CK€n8Ta cHn8neLi1 neTa Jl€Ta CTIIIT8Jlei.1
2.KnaccoB 2.noJ1o)f(€- 2. nOllO>Ke- 2.3aMe-
coeA"'He- Hlllfl ABOi.1- H"' Tpoi'i- cH1Tenei.1
Hlt1M HOL.1 CBfl3111 HOM CBfl3111
B"'A (allKeHbl) 3.KllaccoB 3. KllaCCOB
"'30Mep"'''' 3.npoc- coeA"'He- coeA"He-
TpaHcTBeH- Hlt1f1 H"'i'j (A",e-
HaH (AflH (I1"'KllOna- HOBbie)
ManblX pa<jJ"'Hbl)
I1"'KllOB) 4. npoc-
TpaHCTBeH-
Ha
BCTpeaIOTCH ,lJ,a ,lJ,a HeT HeT ,lJ,a
11'" B
np"'poAe
PacTBo- HeT HeT HeT HeT HeT
plllMOCTb B
BOAe
OTHOW€HIII€ He o6ec-
K OKtIICJ1It1Te- YCTOL.1'-1It1Bbl YCToiii'-lt.1Bbl 06eCLJ,S€4111- 06eCLJ,S€4111- LJ,S€YIt1BaeT,
llHM SaHlt1e BaHllle np" Ham/!-
(p-p KMnO,)- (oKItICn€Hllle) (oKt1Cne- y"," 60KO-
K8'-1eCTS€HHafl HHe) BblX u,eneill
peaKltll1f1 - oKlllcn8-
H"'e
54

npeAenbHble OAHOaTOMHble
CnMpTbl
I C n H 2n + 1 0H I
II1nll1
IR-OH\
OpzanU'LeCKUe 6eUfecm6a, MO.neKy.nbL KOmOpbLX coiJepmam
tjJynKlfuona.nbnyro ZUiJpoKCU.nbnyro zpynny - OH,
.coeiJunennyro c YZ.ne6oiJopoiJnb£M paiJuKa.nOM.
(IIpOU360ihlble Y2Jle60iJOPOiJ06, 6 MOJleKYJlaX KOmOpb£X
amOM 6oiJopoiJa 3a.J1!eUieH Ha ZUiJpoKcozpynny)
pal.\lIIOHanbHaSi
C&o1CTeMaT&o1eCKaR
Ha3eaH",e 
ymeBoAopoAa + on
HOMeHKnaTypa
paA"'Kall + Cn"pT
CH-CH- O H
3 2
ST"'llOBb'i'i Cn"'pT
/"-.
3TaHoll
H YMepat(UIO C mozo KOHIW, ziJe 6JlUJICe rjJYHKI(UOHaJlbHaJl
zpynna. IJ,urjJpoil YKa3b16alOm amOM Y2JlepoiJa, npu KOmOpOM
HaxoiJumCJl ZUiJpOKCU.l£bHaJl zpynna.
yrnepO,AHOrO 4 S 2 I
/ CKeneT3 C:'4 CH,-CH,-CH,-CH,-OH
6yraHoIl - 1
U nOnO)f(eHMe 4 3 2 1
fl30MepMSI VMJlPOKCOrpynnbl CH,-CH,-CH,-CH,-OH
'\ 6yraHOJl  1
KnaCCOB
COeAMHeHM CH s -CH 2 -OH
(npOCTble 3<pIllPbl) 3TlAJlOBbiCi Cnl>1pT
CH,
3 21 1
CH,-CH-CH,-OH
2 - MenumponaHoll - 1
1 2 3 4
CH,-CH-CH,-CH,
I
OH
DYT8HOJl - 2
CH,-O-CH,
J!,IAMenmOBblL.1 acJ:Il1p
0+
0-
HO
I
0+ 0-
HO
I
H
0+ 0-
...HO...
I
R R
. . . BO,lJ,OpO,lJ,Ha51 CB5I3b
cI>3'IeCKe CBOCTBa
1-, TK"n R-OH > TK"n R-H, XOpOWO P B H 2 0
55

I XMMMeCKMe CBOMCTBa CnMpTOBI
1. rOpeHllle <[eM> R, meM 60Jlee Ceem!lU-IeeCR- nJlaJIM,
vepHblu HaJlem - H:OnOmb
C n H 2n + 1 0H + 02  nC0 2 + (n+1 )H 2 0
2. PeaKL\1II1II C Y'faCTllleM BOAopoAHoro aTOMa
OH - rpynnbl
R-O-fH (-O<c-H C6R-3b nOJlR-pU30eaHa - HeH:OmOpaR-
KUCJlOmHOCmb, aUCCOltUalUJl JIWHbWe, lleJJ1 y eoobl.
OH:paCH:U uH8uH:amopa He MeHR-lOm)
3) C 3KTIIIBHblMlil MeTann3MIII
i aJllW20JlJlmbl-
2R-OH + 2Na  2R-ONa + H 2 6elljeCm6a
nenpO"'l7-lble. 6oaozl
R-ONa + H 2 0  R-:OH + NaOH pa3JLUZalOmC.fl
6) C Opr3HIII'feCKIiIMIil KlllcnOT3MIII (3Teplilc!>IIIK3L1111111)
----- H+
CH 3 Co;OH + HOCH 3 -7 CH 3 COOCH 3 + H 2 0
- - - - - t CllO>KHbli'i s<jJ"'p
3. OTl!.\enneHllle OH-rpynnbl RtOH (c ranoreHOBo-
AOPOAHblMIll KlIIcnOTaMIII)
H+
R-OH + HBrR-Br+H20
OW
4. PeaKL\1II1II C Y"laCTllleM OH-rpynnbl III H-aTOMa
coceAHero IIInlll 6nlll>Kalliwero. H
3) OKlllcneHllle (KMnO" K,Cr,O,+H,SO.. O,+kat) R-etOH
  O;8--: ] O
CH 3 - y -OH+[O]..... CH 3 -P:QI::I: +CH 3 -C, +H 2 0
H H H
allb,L\er"'A
6) ,qerlll,qp3T3L1111S1
(r>140°C)
H H
I I H1- _
H-C-C-H  t ' CH,-CH,+H,O C,H,OH:t:H()c-C,H,-c,H,-O-C,H,+H,O
1 1
){ :QH" 3TL1J1eH ,QL13;Bbl
(r<140°C)
56

I
C 2 H s OH
3TaHon. (3TMnOBbIM CnMpT)
8T8Hon,8TunOBbIU cnupT
BUHHblH cnu T
)l(It1AKOCTb,3 xapaKTepHblt.1,
1'=0,8 rjcM 3 , T K "n=78,39°C,
p B H 2 0 It1 OpraHIt1'-jeCKIt1X
paCTBOpIt1TenSlX.
nonY"IeHHe
1. KaTanIllTIII"IeCKaSi rlilApaTaLlIIISI 3TlllneHa
kat - H 3 PO M f260-300°C, p-7 -8 Mna
H+
C 2 H 4 + H 2 0  C 2 H 5 0H
r,p
2. 5pO>KeHllle rmOK03bl (npoAYKTOB,cOAep)l(aLl\l1x
KpaxMan 11 caXapl1CTble BeLl\eCTBa).
cPepMeHTbl
C 6 H 12 0 6  2C 2 H 5 0H + 2C0 2
CTpoeHHe
IS- I /)+
Of-l-H
I
CH s - CH 2
/)-, /)+
H - Olf- H
I
BnHRHHe paAHKana Ha
nOABHJKHOCTb BOAopOAa
3n€KTpOHHafi nnOTHOCTb cMew.eHa K
KcnopOAYJ HO paKan OTTanKBaeT OT
ce6H e. CMeLl1eH"'e slleKTpoHHoi'i
nnOTHOCTIII nplllBOAIIIT K YM€HbW€HlllfO
nonflpHOCTIII CBfl3111 a-H, nOJJ.,BI1}KHOCTb
BO,l\OpOAa B rl'lAPoKcorpynne y cn"'pTOB
YMeHbwaeTCSI.
Y aTOMa KL-ICnOpOAa B MoneKYne CnL-lpTa Sp3 fL-l6pL-lAL-I3al\L-IfI.
BaneHTHbI LC-O-H=106" W
AeHaTYPL-lpoBaHHbl CnL-lpT = 3TaHon c npL-lMeCmylL-1. "A"
(AeHaTypaT)
57

nplllMeHeHMe npeAenbHblX
0AHOaTOMHbIX CnlllpTOB

1. cPJ//3J//'-IecKJ//e CBOiltCTB8
)l(It1AKOCH1, paCTBOplt1Mbl B H 2 0
It1 OpraHlt1yeCKIt1X paCTBOpIt1TeJlX
PaCm60pUmenu, amanon->iJyxu,
neRapCm6a, CnUpmnbte nanum"KU
2. rOpeHJ//e
2CH 3 0H+30 2 =2C0 2 +4H 2 0+Q
C 2 H s OH+30 2 =2C0 2 +3H 2 0+Q
rOplO'tee iJnH iJ6uzameneu, iJo6a6"Ka
"K wmopnoMY monnu6Y
3. B38J//MO/l,eiltcTBJ//e C ranoreHOBO/l,OpO/l,8MJ//
C2HsOH+HCI=C2HsCI+H20
XJlOpSTaH
Pacm6opumenb, C2HsCl- MecmHaH anecmeaUH
4. /l,erJ///l,p8TaL/J//fi
C 2 H s OH+HOC 2 H s  C 2 H s -0-C 2 H s +H 2 0
MeiJulfUnC"KUU atjJup, nap"Koa
5. OKJ//cneHJ//e .P
C 2 H s OH+[0]  CH 3 -C" + H 2 0
H
o 0
-7 -7
CHs-C" +[0]  CHs-C" + H 2 0
H OH
YKCYCHaS1
KlllcnOTa
llonY'tenue nUUfeeou Y"Kcycnou KUCnOmbt
58

Cnoco6bl nony...eHIllSi CnlllpTOB
1. (UenO'lHbIM rHAPonHa ranoreHanKaHOB
KOH
C 2 H s CI + H 2 0  C 2 H s OH + HCI
2. rlll1ApaTa4HSI anKeHOB (npaBl1nO MapKOBHI1KOBa)
CH 3 - CH = CH 2 + H 2 0 = CH 3 - CH - CH 3
npon"'1l8H I
OH
nponaHOll-2
3. BoccTaHoBneHHe KHcnopoAOCOAep>KaHX
coeAHHeHHM (an bAerlt1)J,OB , KeToHoB)
'i- 0 Ni
CH -CH -C + H -7CH -CH -CH -OH
3 2 '- 21' 3 2 2
H
4. 6pO>KeHHe I"nIOKOabl (cpepMeHTaTIt1BHoe) -
TonbKO AnSI 3TaHona
q,epMeHTbl
C 6 H 12 0 6 = 2C 2 H s OH + 2C0 2 t
5. ilia CHHTea,-raaa - TonbKO AnSI MeTaHona
(r 200-300T, p=6-8 Mna, kat CuO, ZnO, A1203)
 O + 2H q = CH 3 0H

CMHTe3-ra3
59

InpeAenbHble MHOrOaTOMHble CnlllPTbil
CoiJep3/Cam 6 MOlteKylte HeCKOltbKO ZUiJpOKCUltbHbtX zpynn
npOCTeHWllle ,LjBYX- Cnl1pTOB TpeX8TOMHbiX
npe,qCTaBIllTenlil CH 2 -CH 2 CH 2 -CH-CH 2
I I , 1 I
OH OH OH OH OH
STaHA"Oll - 1,2 nponaHTp"oll - 1 ,2,3
3T111lleHrnlllKonb nponlllneHrnlllKonb
m"l1ep"'H
OC06eHHOCTlil CTpOeHIIISI OH - zpynna lluxoiJumcR, npu
pa3ltu'tllbtX YZltepoiJHbtX amOM/LX
cJ>1II3111'feCKlile CBOHCTBa B.R3ICUe cuponoo6paSIlbte JlCu8KOCmu,
 \. cJ/.a8Ko6amozo 6Kyca, xopowo
p 6 H20 T,wII »T,tlmn.oH
(sa C'lem 6080po81lbtX C6.RSeu)
amUJ/.eIlZJ/.UKOJ/.b - R,iJo6um
XIIIMIII'feCKlile CBOHCTBa CxOiJHbt co C60ucm6uMu
oiJHoamOMHbtX cnupm06
llpu peaKqU.RX .MOJICem y'tacm606amb KaK 081/.a,
maK u 6oJ/.ee ZU8POKcozpynn.
Ka'feCTBeHHaSi p eaK Ll IIISI- 6sauMoiJeucm6ue C ZUiJPOKCUiJOM
M,CiJu (II).
2NaOH + CuS0 4 Na2S04 + Cu(OH)).
1I136blTOK HeCK. Kanenb
CH -OH CH2-0....CHO-CH2
I 2 I U I
CH -OH + CU(OH)2 CH-O': ....O-CH +2H 2 O
I I H I
CH 2 -OH CH 2 -OH HO-CH 2
rll"'l1epaT MeA'" (II)
SaClllnbKOBbll:1 paCTBOp
nplilMeHeHllle 3TI1fleHrfll1KOflb rfll1L<epl1H
aHTII1cpPll13, B OpraHIt1- B napcplOMepHOW, cpapMau.eBTII1-
4eCKOM CIIIHTeae l.jecKoiil, rel(CnmbHoil! npoMblwneH-
Hocn1, CMftr41/1Tenb KO)/(I/I It1 TKaHei1,
BB (H"TpocoeA"HeH"H)
60

npOCTble 3Mpbl
IIpocmbte 3q.'1pbt - opzauu'£eclCue coeiJuueUlUt
cocmaea R-O-R', ziJe R u R' - oiJuualCoebte unu
pa3nU,£ubte yzneeoiJopoiJubte paiJuICanbt.
n arjJup n
HOMeHKnaTYpa YZJle6oiJopoihlble paiJwWJlbl U
HaSblBamb c npOCmeUUleZO. EC.ftll R OOUllalCOBbl. mo npUCmaB1-ca iJu-
CH 3 -O-C 2 H s C 2 H s -O-C 2 H s
MeT"'llST"'llOBb'i'i S<jJ"'p A"STI,1110Bbli'i S<jJ"p
nony'feHllle
1. llpu lwzpe6wlUu cnupm06 (+H 2 S0 4 (KOlll{.))
H,SO,(K)
2C 2 H s OH  C 2 H s -O-C 2 H s + H 2 O
t<140'C .
2. llpu 63au.M.oiJeucm6uu aJlK02QJlJlm06 c
zaJloze1lnpOu36oiJllbiMU
C 4 H g ONa+C 2 H s Br  C4Hg-O-C2Hs + NaBr
3T"'1l6YT"'llOBb'i'i s<jJ"p
MeHee peaKlifOHOCnoco6Hbl, ..,eM cnlifpTbl.
He pa3naralOTcR Hlif BOtlO;;;, Hlif UlenO'IaMIif,
XapaKTepHaSi peaKSI - c iOioAOBOAoPOAHOiii KIIICllOTOiii (KOHl\.)
C 2 H s - 0 - C 2 H s + HJ-> C 2 H s J + C 2 H s OH
C 2 H s -O-C 2 H s )l(I1AKOCTb, , 3 xapaKTepHbliii,
AST"llOBbli'i a<Pp . TK"n=35 ,6°C
cepHbli'i 3<jJ"p nO>KapOOnaceH.
M€'!\"l1"'HCK"'i'i s<jJ"p
nplilMeHeHllle
PacmeOpUmeJlb opzanU'leCKUX eeU{ecme, e MeiJUltUne -
llapKOmU'leCKOe cpeiJcm60 (allecmeauJl).
61

CbeHonbl
c])elWJI,b£ - ZUBPOKCUJI,bnb£e npoua6oBnb£e apOMamU'£eCKUX
YZJI,e6oBopoBo6, 6 MOJl,eKYJl,aX KOmOpb£X tjlynKlfuonaJl,bnb£e
zpynnb£ C6R,aanb£ C 6enaOJl,bnb£M R,BPOM.
OH OH OH OH OH
A ACH 3 A HOh oH
VV VOH V
cPeHOll OpTO-KCII1HOll
\. .I
V
OAHoaTOMHble cPeHOllbl
C 6 H s OH
111m'!
OH
@
<jJeHOI1
Kap60110BafJ
KtIICJlOTa
OH
n1ApOXII1HOH pe30pL\IIIH
\. j
V
AByxa-rOMHble cPeHOllbl
nlllporaIlllOll
 J
V
TpexaTOMHbl cPeHOll
cJ>1II3111'feCKlile CBOCTBa
TBepAoe KpWCTannW4eCKoe Be14eCTBO,
(OKWCmJ5JCb Ha B03Ayxe - p030BbIM),
3 pe3KWCi XapaKTepHblCi, T n "=42"C, T,"n=182"C,
M paCTBOpWM B H 2 0, cwnbHblCi aHTwcenTWK,
H,[IOBIilT.
-
-
"
C 6 H S - paAIIIKan c):>eHllln
8-
O@-9+-H
8-
C 6 H S - YBell"'"'BaeT
nOAB"'>KHOCTb aTOMa
BOAopOAa r"'APoKcorpynnbl
,
R--+O-';H
'. ,
-C 2 H s ( -CH s ) YMeHbwaeT
nOAB"'>KHOCTb aTOMa
BOAopOAa r"'APoKcorpynnbl
62

XMMWieCKllle CBOMCTBa cl>eHOna
-OH no zuiJP01\'cOZpynne
Boapacmaem IWCJWnUlOCmb OH-zpynnbl. rpelio.n - 6o.nee
c.na6aR. Kuc.noma, "eM H 2 C0 8 , IiO 60JiCe CU.nb/laR., "eM R-OH.
1. C aKTIIIBHblMIil MeTannaMIil
2C 6 H s OH + 2Na = 2C 6 H s ONa + H 2 i
<jJeHollSIT Na
2. Co lJ..1,enOQaMIil
C 6 H s OH + NaOH -----7 C H aNa + H 2 O
6 S
TBepAoe £136bITOK paCTBopfleTCfI
rpe/lo.nJlntbl JieZKO paa.nazGlomcR. c"a6butU Iwc.nomaJlw.
C 6 H s ONa + H 2 0 + CO 2 = C 6 H s OH + NaHC0 3
3. C ranoreHonpOlll3BD,I:\HblMlil
C 6 H s OH + C2HsJ C 6 H s -O-C 2 H s + HJ
sT"'1l<jJeHI<1J10Bbl s<PP
4. Co cnlllpTaMIil
(06pa30ealiue npocmblX U CJ!O:JfClib!X apupoe.)
.-- ------.-.-.
:OH
@"'.:O - C 2 H s -7@Jo- C 2 H s + H 2 O
KaQeCTBeHHaH D eaK U IIIH C H - 0 - C 2 H s
6 5
- eBauMOaeucmeue C x.nOpUaOM :llCeJle3a (III).
@. @
0 0
3C 6 H s OH + FeCl s , / +3HCI
-7 Fe
1
0
<jJeHollT >KelleSa @
Kop"'HeBo-<jJ"'olleToBblj;j pop
C sanaXOM TYW'" (KpacK"')
63

XIIIMlllileCKllle CBOMCTBa cl>eHona
@
IIoo OCUCm6UCJIl a.nCKmpOH1WU napbl amoJila ICUc.nopooa
60SpaCmacm a.nClCmpOHHaJl n.nOmHOCmb
6 ICO.nblfC.6 no.nOJ/CCHUU 2, 4, 6.
no 6e1£30Rbl£OMY lWRblfY
OH
'J'
1)-
1)-
1. C 6POMHOM BOAOM (6e3 t n III kat)
OH
o
+ 3Br 2
OH
Br I 
h-
Br I
t + 3HBr
Br
2, 4, 6-mpu6poMpCHO.n
2. C a30THoM KlllcnoToM
OH
o
OH
N02 0 N02
+ 3HON0 2 = I + 3H 2 0
h-
N0 2
2, 4, 6-mpuHumpopcHo.n
(nlllCpuH06aJl lCuc.noma)
64

AnbAerlllAbl. CTpOeHllle.
HOMeHKnaTYpa. M30Meplll
AnbAerl1Abl - OpraHI14eCKI1e
Bell.\eCTBa, MoneKynbl KOTOpblX
COAep)\(aT Kap6oHI1nbHYlO
rpynny (_C:"O), COeAI1HeHHYIO
C yrneBoAopOAHblM paAI1KanOM
11 aTOMOM BOAOpOAa.
Spz rI16pI1AI13al\I1, BaneHTHbliiL120°, BCe O(Cl1rMa) CB31i1
ne)\(aT B OAHOii nnOCKOCTI1, n(nl1) - CB3b 1.. nnOCKOCTI1
,I:i' iC\F , n /
/C I:i 0 /C I:i C,
KOBaneHTHa
nOnpHa HenOnpHa
3a C4eT pa3nl14Hoi1 3.0. aTOMOB C 11 0
BnuJ£uue amOMa xucnopoiJa 6 xap60UUfl,bUbtX coeiJune-
UURX nepeiJaemcJt no Ifenu => J<ap60UUl!buaJt zpynna o6YCl!a6-
/l,U6aem 6b£COXYro peaKlfuouuyro cnoco6uocmb aJl,bOezuiJo6.
R_CO
'H
HOMeHKmrrypa
CH _C'i O
3 ....H
ucmOpU'LeC1WJt
113 Ha3BaHI1
KI1CnOT
cucmeMamU'LeCKUJl,
A
yrneBoAopoA + anb
YKCYCHblii 3TaHanb
-llepe8 KOpHeJn HLl36alillJt 3anUCbll3a101n 601f0{3blC 3aMecn1unWJlU
C y,w3aHueM ux noJlO:JICeHllJt II 'lllCJla. HYMep a 4 w ,
anWMO{3 YZJlepo8a lia1lUHBenlC,f{, c -,cap60liUJlbln1-l0u. zpynnbl.
4 3 2 1 ",0 .
CH,-yH-CHz-C, H 3 - MeT"'1l6YTaHallb
CH, ("'30BallepbHoBblj;i allbl\er"'A)
yrnepo,qHoro CKeneTa
I . OS 2 '0
CH,-CHz-CHz-H CH,-CH-C:: H
W30MeplllH 6YTaHa"b C ' H
\ 3 2-MeTItI.nnponat!811b
KnaCCOB COe,qIllHeHIIIM C"H,"O O il
(KeTOHbl)
CH,-CHz-CO H CH,-C-CH3
nponaHOH(aeTOH)
.....-'---.r-'--.,....-J--., npOnBHBJ1b .....
anbAerl1A - Cnl1pT, nl1WeHHbl11 BOAopOAa
65

CbopManbAerlllA.
nonyeHllle. CBOMCTBa
H-CO
'H
<jJopMallb,L\er"A
MeTaHanb
MypaBbtllHbli1 anbAert1,l],
30-40% p-p - <jJopMall"'H
1,4,. 3 pe3KI-1i:1 XapaKTepHbli:1,
B H 2 0 P XOpOWO
Ae3I-1H<pI1L\l-1pYIOLi\ee 11
KOHCepBl-1pYIOLi\ee CpeACTBO
nOnYLleHllle OK"'CfleHl1e MeTaHona
Kl1cnOpOAoM B03Ayxa B np",cYTCTB"'''' kat.
kat
2CH 3 0H + O 2 ---7 2CH 2 0 + 2H 2 0
Ilp0R,eJl.R,em o6Ufue ceoucmea aJl.biJezuiJoe.
Oco6ble caoiiicTla
1. CaMOnpOl.-13BOnbHafl TpIllMepI13aL\l1f1
CH,
/' "-
3H-C 0 0
- I I napacpopManbAerE>1)J.
(TptllOKCtllMeTII1J1eH)
H,C CH,
"- 0 /'
2. B3aI1MOAei:1cTBllle C aMMl1aKOM
/""'-
H,C CH, CH,
I 6CH 2 0+4NH 3 -I "N.... CH I +6H 2 O
CH 2 2
N" ....N
" /reKcaMen,meH-TerpaaMt1H
CH 2 (ypOTpon"H)
3. Co 14enOyaMI1 OKI1CnfleTCfI 11 BOCCTaHaBnl1BaeTCfI
OAHOBpeMeHHO
2CH 2 0 + KOH - CH 3 0H + HCOOK
66

CBOMCTBa anbAerlllAOB
cJ>1iI31i1L1eCKHe C , -I, C 2 -C S - )l(I1AKOCTI1, BbICWllle-TBep-
CBoi'icTBa Able, Ha'mnbHble npeACTaBI1Tenl1 p B H 2 0,
C pOCTOM R P naAaeT (HeT BOAOPOAHblX
CBf!3ell1), T nmaJIb < T KI1f1 ROH
XHMIiILleCKHe
CBoi'icTBa
'1eM 60nbwe 1)+ Ha aTOMe C, TeM Bblwe
aKTI1BHOCTb.
I. PeaK41i11i1 nplilcoeAIiIHeHIiISI
1) C BOAOPOAOM (to, kat Ni I1nl1 Pt)
-<,,0 r
CH 3 -CH 2 -C, + H 2 ---? CH 3 -CH 2 -CH 2 OH
H NI nponaHoll-1
2) co Cnl1pTaMIII, o6pa3Y aL\eTanlil (kat H+)
OC 2 H s
-<,,0 H. I
CH 3 -CH 2 -C + 2C 2 H s OH -7 CH 3 -CH 2 -CH + H 2 O
'H I .
OC 2 H s
II. PeaK41i11i1 oKliIcneHIiISI - KalJeCTBeHHbie p eaK LJ. 11111
1) peaKl\lII "cepe6pHoro 3epKana" (B3aIllMoAeVicTBllle
C aMMI1a4HbiM paCTBOpOM OKCI1Aa cepe6pa npl1 r)
-<,,0 r -<,,0 t
CH 3 -C + Ag 2 0 -7 CH 3 -C +2Ag
'H NH,OH 'OH I
YKCYCHafi KII1CJ10Ta
2) C rl1APOKCIIIAOM MeAI1 (II) npl1 1"
-<,,0 r 'i O t
CH 3 -C + 2Cu(OH)2 -7 CH 3 -C + 2CuOH + H 2 O
- 'H C"H"i'i 'OH >KellTbli'i
r
2CuOH -7 Cu 2 0t + H 2 O
KpaCHblill
III. PeaK41i11i1 3aMellleHIiISI B R C ranoreHaMIiI
(mOM BOAopOAa npl1 BTOpOM aTOMe C 60nee nOABI1)1(eH)
'l0 -<,,0
CH 3 -CH 2 -C + Br 2 -7 CHs-CHBr-C +HBr
'H 'H
67

CBOMCTBa anbAerHAOB
(npOAOn>KeHMe)
I. nOnMMepM3a4MSI cJ>OpManbAerMAa
nCH 2 0 -7 (-CH 2 -O-)n KpIt1CTan. B-BO, \
nOll"<jJOpMallbAer"A MeXaHIt14eCKa5J np04HOCTb,
(nOll"OKC"MeT"lleH) XOPOWI1L1 Ll,113neKTp1t1K
8 OTnl1411e OT 3TI1neHOBbiX OTHOCI1TCfI K reTepo4enHbiM
nonlilMepaM (MaKpoMoneKyna COLl,ep)l(l1T aTOMbl ABYX
Tlt1nOB: ymepoLl,a 11 KIt1CnOpoAa)
II. nonMKoHAeHca4MSI* c cJ>eHonoM (nonY4eHlt1e
cpeHonnacTOB)
cPeHonnacTbl - TepMopeaKTMBHble nonMMepbl (He nnaBflTCfI npM r)
-,,0
H-C'" + H+ -7
'H
+....OH
H-C
'H
OH
o
OH
+ H-C,H  O-CH,oH + H'
. OH
 OCH,- "+ "H,O
OH
"OCH,OH
cpeHon-cpopManb.n,enl/l,Ha51 CMOna
npt1 t136b1TKe cPeHona - HOBOnal.jHafl CMona,
np" !,136b1TKe cpopMaJlb,L\er"Aa - peS"T
* PeaKL\IIIH 06pa30BaHlilSi nonlilMepOB, KOTopaH
conpOBO>K,qaeTCSI Bbl,l],eneHllleM HlII3KOMoneKy'nSipHoro
npOJ:\YKTa (H 2 0) - peaKL\IIIH nonIllKOH.qeHCaL\lIIlII.
68

c
KeTOHbl
r.
o
II
R-C-R Y
KeTOHbl - OpraHl1yeCKl1e Bell.\eCTBa,
MoneKynbl KOTOpblX cOAeg>KaT
Kap6oHI1nbHYlO rpynny (-c:: ), coe-
AI1HeHHYIO C ABYM yrneBoAopoA-
HblMI1 paAI1KanaMI1.
paL\IIIOHanbHaSi
CIilCTeMaTIII'IeCKaH
/\
ymeBQAOpOA+OH
HOMeHKnaTypa Ha3BaHI1e paAI1KallOB
+KeTOH
CH 3 -C - CH,-CH 3 MeTl1n3T"'llKeTOH
II
o
ljUljJpa 6 KOlilje lia36aliUR YKa3b16aem nOJlO:I/CeIiUe 6 ljenu amOJna
YZJlepo{Ja, C KOmOpblM C6.wJaH Kap60HUJlbHblU KUCJlOPo{).
HYMepaljUIO ZJla6HOU ljenu Ha'lUlialOm C
6l/.u:HCaumeZO K Kap6oHUl/.bHOii zpynne KOHlfa.
6YTaHOH-2
yrnepo,qHoro CKeneTa
/ 1 2 34 5 1 23 4
u CH 3 -CH-C-CH,-CH 3 CH 3 -C-CH-CH 3
r.30MeplIISI II II 1
\ 0 0 CH 3
neITaI-iOH-3 3-Men1I16YTaHOH-2
nOnO>KeHllle K3p6oHlllnbHOrO KIIIcnopo,qa
CH 3 -C-CH,-CH, -CH s CH 3 -CH, -C-CH, -CH 3
II II
o 0
neHTaHOH2
1l6HT<J.HOH-3
Cl>1II3111'1eCKlile npocmi-iwl1e - )!("'AKOCTI1, , 3 XapaKTepHbli-i,
CBOMCTBa p B H,O, BblCWl1e - TBepAble B-Ba
XapaKmepUb£ MUOZUe XUMU<LeCKUe C60u.Cm6a al/.bOeZU006.
OKUCJleliue 3IW'iUmeJlbHO mpy{JHee, C pa36b160M YZJlepo{J/fDU lienu,
He 6cmynaJOm 6 peaKlfuJO "cepe6pJtHOZO 3epKal/.a."
AL\eTOH (nponaHOH, <;(
AI1MeTl1nKeTOH) CH 3 -C-CH 3
>KI1,[\KOCTb, , 3 pe3K11i-i xapaKTepHbli-i, T",=56,2T,
p B H,O XopOWO, paCTBOp"'Tenb OpraH",yeCK£1X Bell.\eCTB
69

I nonY'feHllle anbAerlllAOB III KeTOHOBI
1. OKMCnetiMe cnMp"roB(O, Ha,lJ, Cu, K,Cr,O"KMnO" CuO)
=H
. i -. .. : _ t' 'i O
R - .<? - OH + CuO  R-C" H + Cu + H 2 0
H nepBIIIYHble  anb,Qerlll,lJ,bl
BTOpl1YHble  KeTOHbl
2. ilia MeTaHa(r-500.C, kat - OKCW,lJ,bl a30Ta)
t. ",,0
CH, + O 2  H 2 0 + H-C
kat ........H
I{) PeaKl.!,&1M KY"IepOBa (1881 r.) - rl1L\paTal(I1f1 al(em-
neHa B npl1CYTCTBl1111 coneti pTYTIII (Hg 2 +)
[ l 9 H J t. "",0
CH=CH + H 2 0 -7 CH . 2 = C -7 CH 3 -L
I Hg+ ........H
H
BItIHliIl1DBblt1 Cnll1pT
(HeycToi.1....I.1B)
_ npl1 rlllApaTal(11111 roMonoroB - KeTOHbl.
(41 OKMCneHMe 3TMneHa (kat-xnOpIIIAbl Pd 11 CU)
\...... kat 'iO
2CH 2 = CH 2 + O 2 -7 2[CH 2 =CH-OH]  2CH 3 -C
"H
 ilia anKeHoB-oKCocMHTea (kat -KOMnneKCHble
coeL\-fI Co, p=5-10Mna)
CH 2 = CH 2 + CO + H 2  CH -CH -c""O
3 2 "H
6. ilia AMranoreHaaMeUl,eHHblx anKaHOB (rl1L\pOnI13)
I CI
r
CH 3 - « - H
I CI
N alo H
. ",,0
+  CH 3 -C"H
N aJ OH
+ 2NaCI + H 2 0
nepBIIIYHble  anbAerlllL\bl
BTOpl1YHble  KeTOHbl
70

Kap6oHOBbie KMCnOTbl.
rOMOnOJ"HLleCKHM PSiA
R-CO
'OH
-::;-0
-c I-1nl-1
'OH
Kap6oHOBbie KWCnOTbl - OpraHW-
4eCKWe COeAI1HeHW51, COAep)l(all.\l1e
OAHY wnl1 HeCKOnbKO Kap6oKCWnb-
HblX rpynn, COeAI1HeHHblX C
yrneBoAopOAHblM paAI1KanOM.
-::;-0
Kap6oHI1Jl -C
,
-COOH +
rl1APOKCIt1Jl -OH
Kap6oKCI1JlbHa51 rpynna
CnH2n+1COOH 0
""
"11" OCHOBHOCTb = 411CJlO - C rp y nn
.....OH
C n H 2n 0 2
npeAenbHble OAHOOCHOBHble
Kt1CJlOTbl
"3 Ha3BaH"ti
npOCTeI1W"'X
KI-1CllOT

npOn"OHOBa npOnaHOBa MeTl1f1YKCYCHa
Hyillepal-lUJJ amOM06 YZJl€poiia 6 lIenu Ha'lUHalOm C
Kap6oKCUJlbHOil zpynnbl.
/ yrnepO,qHOrO CKeneTa C>4
CH 3 -CH 2 -CH 2 -COOH CH 3 -yH-COOH
(.130Mep1IISI 6YTaHDBaO (MacnOHao) CH
KMcnOTa S
\ 2-MeTnnponaHoea
(30MaCfiHa)KcnOTa
Kl1aCCOB coe,qIllHeHwH C n H 2n 0 2
(cnO)f(Hble S4>\I1pbl) 0
CH - CH _ C ""O CH3 -C
3 2 'OH p-CH 3
npOnaHOBaS! KL1CllOTa Men1flObllt1 3Q:lMP
YKCYCHOVI K\I1CIlOTb!
HOMeHK113Typa
321
CH 3 -CH 2 -COOH
MCTopeCKag CCTeMaTHeCKag paQOHabHag
(Tp"B"allbHoe
Ha3BaH"e)
allKaH+OB3S1
K"'CllOTa
71

HeKOTopble npeAenbHble
o HOOCHOBHble KIIICnOTbl
<POPMY JIa Ha3BaHHe
no CIiCTeMflTllQeCKOH T....m,DC
TpHBllaJIbHoe HOMeHKYJIaTVUe
HCOOH MypaBbIIHa.H MeTaHOBa.H 101
CH3COOH Y KCYCHa.H :''lTaHOBa.H 118
C2H5COOH IIporrIIOHOBa.H IIporraHoBa.H 141
C3H7COOH MaCJI.HHa.H BYTaHOBa.H 163
C4H9COOH BaJIepb.HHOBa.H IIeHTaHoBa.H 186
C5Hl1COOH RarrpOHOBa.H reKCaHOBa.H 205
C6H13COOH 8HaHTOBa.H rerrTaHOBa.H 223
...... . .... ... ... .. . . . .
C15H31COOH IIaJIbMIITli - IIeHTa,iWKaHOBa.H TBep-
HOBa.H .n;ble
C16H33COOH MaprapliHOBa.H reIWa.n;eKaHOBa.H B-Ba
C17H35COOH CTeapliHOBa.H rerrTa.n;eKaHOBa.H
72

I Kap6oHOBbie KIf1CnOTbl. CBOMCTBa I
ct>M3M'IeCKMe CBOMCTBa
HeT ra30B, K"'CllOTbl HOpMallbHoro CTpOeH"' OT C, ,L\O
C, - )I("'AKOCT"', );" 3 pe3K"'i'i, C C, - TBepAble. PaCTBOp"'MOCTb
B H,O: nepBble TP'" - B ll106blX OTHOWeH"'X, nOClle,L\YIOU\"'e -
- OrpaH"'eHO, TBepAble - npal<T"'eCK'" H. T,," '" paCTBOp"'MOCTb
B H,O 6011bWe, eM y Cn"'pTOB, allb,L\er"'AOB, allKaHOB.
1)- 1)+
0... HO
-::::-
R-C  1)+ 1)- -::::- C-R
OH...O

A"'Mepbl
"H" -CB3b
1)
1)+ ('0
-::::-
R-C  ..
"-9  H
BmllSlHllle Kap6oHlllnbHoiii rpynnbl
ATOM C, npMo6peTa 1)+ (3a C'feT nOnpHOCTM CB3M C=O),
np"'Tr"'BaeT e r"'APoKcorpynnbl. CB3b O-H
nOllpM3yeTc --7 H - 60nee nO,qBIII>KeH.
S3a"'MHoe Bll"'H"'e
aTOMOB B MOlleKYlle
BnlllSlHMe rlll,qpOKClllnbHOH rpynnbl
3a C'feT e r"'ApoKcorpynnbl '1aCT""JHO raC"'TC
1)+ aTOMa C M peaKL\1II1II nplllcoe,qIllHeHIIISI
no CBSl3111 C=O 3aTpy,qHeHbl.
XMMM'IeCKMe CBoMCTBa
oco6ble CBOHCTBa KaK MHHepanbHble
3Tep/llcp/llKa,-//II/II ,l1/11cco,-//IIa,-//IIfI B BO/1,HOM
(co CJl/11PTaM/II)  I pacTBope
no pa,l1/11KaflY  _____ C MeTaflflaM/II
o6pa30BaH/IIe . KiIIcnOTa_ C OKClII/1,aM/II MeTaflflOB
aHr/ll,l1p/ll,l10B /  C OCHOBaH/IIflM/II
peaKlJ,/II/II BOCCTaHOBfleH/IIfI --------.. C COflflM/II
73

I
X.....M........ecK.....e CBOVlCTBa npeAenbHblX
0AHOOCHOBHbIX Kap6oHOBbiX K.....CnOT
1. Accol..!,al..!,SI B BOAHOM pacTBope.
CJla6ble 8JleKmpOJlUmbl. OKpawu6alOm uliiJuKamop.
CH 3 COOH  H+ + CH 3 COO-
2. B3aMoAeitcTBe C MeTannaM
2CH 3 COOH + Mg = (CH3COO)2Mg + H 2 i
al18TaT MarH"'''
2H+ +Mg o =Mg 2 + +H 0 2 i
3. B3aMoAeitcTBe C OCHOBHbIM OKCAaM
2C2HsCOOH+MgO=(C2HsCOO)2Mg+H20
npon"'aT MarH"'''
2H++MgO=Mg 2 ++H 2 0
4. B3aMoAeitcTBe C OCHOBaHSlM
CH 3 COOH+KOH=CH s COOK+H 2 0
al1eTaT Kall"'''
W+OH-=H 0
2
5. B3aMoAeitcTBe C conSlM
2CH 3 COOH+K 2 C0 3 =2CH 3 COOK +H 2 0+C0 2 i
2H++CO 2-=H O+ C . 0 i '
S 2 2
6. B3aMoAeitcTBe C aMMaKOM (KaK oCHoBaHeM)
CH 3 COOH+NH 3  CH 3 COONH 4
al1eTaT aMMOH"'''
jJ t" jJ
CH 3 -C "  R-C ,-,
O-NH 4 -H 2 0 I\JH 2
aM"'A
74

,
,
,
X.....M........eCK.....e CBOMCTBa npeAenbHblX
OAHOOCHOBHbiX Kap6oHOBbiX K.....CnOT
(npoAOn>KeHllle)
1. PeaKLlIIISI 3Teplll(j>IIIKaLlIIIIII - B npl1CYTCTBl111
Cl1nbHblX HeOpraHWJeCKMX KMcnOT
CH C jJ +HO-CH !:4 CH -C jJ +H 0
3 ,.____:. 3 3, 2
OH : O-CH
..". . .." 3
MeT"'lloBbli'i S<jJ"'p
YKCYCHOi'i K"'CllOTbl
" 2. 83aI1MOAeL1CTBl1e C BOAOOTHI1MalOLl\MMM
areHTaMI1 (P20S) - o6pa30BaHlile aHrIllAPIilAoB.
jJ O jJ O
R-C + C-R'  R-C-O-C-R' + H 2 0
'OH. .H:O aHr"'AP"'A
3. PeaKL.\I1M 3aMeLl\eHMSl - no yrneBoAopoAHoMy
paAIilKany (y 6nM)j(aL1Wero K Kap6oHl1nbH0L1
rpynne aTOMa yrnepoAa).
13 a 13 a
CH 3 -CH 2 -COOH+CI 2  CHs-CH-COOH+HCI
I
CI
2-xllOpnpOnl<10HOBa<1 K"'CllOTa
HaI£U'lUe zal£ozeua 6 (J.-nOI£O:JICeuuu YCUl£U6aem cmeneub
iJuccOlfuaq,uu RUCl£om.
H H
I jJ I jJ B 100 pas
H - C - C CI f-- C f-- C C"'llbHee
I 'O-H I '\ YKCYCHOi'i
H H O-H
YKcyCHa
XllOPYKcyCHa
4. BOCCTaHOBneHllle III KaTanIllTW.IeCKOe rlllAplllpo-
BaHlile (c 60nbwMM TPYAoM).
jJ H jJ H,
C 2 H s -C -H> l ) C2Hs-C  C 2 H s -CH 2 -OH
'OH 'H
75

nonY"leHlf1e Kap6oHOBbiX KIf1CnOT I
1. OKlllcneHllle anbAeJ'"IIIAoB
B Jw6opamopuu - AgzO(aMJltUa'l1ibtu), Cu(OH)z. to
B npOJltbtlUJteHHocmu - Oz, kat
",,0 + [0] ",,0
R-C -7 R-C
'H 'OH
811b,l],erlt1)J, KIiICJlOT8
2. OKlllcneHllle nepBW.IHbIX cnlllpTOB
R-CH 2 -OH + O 2  ",,0
R--C + H 0
P"> I' 'OH 2
SOKlllcneHllle anKaHOB (kat-cOeAI1HeHI1S1 Mn)
kat .::;.0
2CH 3 -CH 2 + CH 2 -CH 3 + 50 2 -7 4CK 3 -C + 2H 2 O
I',p 'OH
4. 1113 cone Kap6oHOBbiX KIIICnOT (na60paTOpHbliiJ
I' cnoco6)
CH 3 COONa(TB.)+H 2 SO. (KOHI1.) -7 CH 3 COOHi +NaHS0 4
5. nonY"IeHllle npocTeWIIIX Kap6oHOBbiX KlllcnOT
(M.6epmo)
200"C.P H,sO
CO + NaOH -7 HCOONa -7' HCOOH
OKCIiIA c:j)OpMIA8T Na MvpaBblllHafi
yrJlepO,lJ,8 (II) KIIICJ10Ta
6. rlilAPonlll3 HIIITplilnOB (R-C=N)
H'
CH 3 -0= N + 2H 2 0 -7 CH 3 -COO H + N H3
au.eTOHi-nplllll t YKCYCH851
KII1C1l0Ta
 Kap6oHlllnlllpOBaHlile anKeHOB (Ha'lI1HaSl C
npOnl10HoBoiiJ) kat H 3 P0 4 , r 300-350°C, p20-30Mna
Ct!3
H' I
CH 3 -C=CH 2 + CO + H 2 0 -7 CH 3 -C-COOH
I I',p I
CH 3 CH"
2-MenUmpOneH 2,2-AIIIMen1IlnpOnaHOB8S1
KIi1CJ10Tf1
76

OTAenbHble npeACTaBIf1Tenlf1
Kap6oHOBbiX KIf1CnOT
/ npeAenbHble }
no R
Knacct(I)IIIKaL!,IIISlS:: HenpeAenbHble
KIIICnOT  apOMan1'feCKWe
no Konlll.."eCTSY
OAHOOCHOBHble } <!>YHK""OHanbHbIX
MHOrOOCHOBHble rpynn _C",O
'OH
 >K"'AKOCTb,  3 OCTpblL1, P B H 2 0 XOpOWa5l,
T,,"=100,TC
OH Ka'feCTBeHHaSi peaKLlIIIH - peaKLI,wH
MypaBbwHa51 "Cepe6p5lHoro 3epKana"
(MypaBb"', ",,0 .. ",,0 t
ellb, Kpan"'Ba) H - C + A9 2 0 ---t OH-C +2Ag
....OH NH.oH ....OH
A 
np'" nonaAaH"'W Ha H2CO
1<" ...,.
KO>KY - O>Korlil. HO CO
06Jtaaae1ll 6alU1U'pl{.l1l{J1ibUlU c6uikm(ja.MU, lCOlicepeaum.
"",0 >K"'AKOCTb,  3 pe3K"'L1 XapaKTepHblL1,
CH:'-C T,""=118,1" ,np", r 16,75"C 3amepAeBaeT,
3 ....OH 06pa3yS1 KpWCTallnbl (neJ],5lHa5l),
YKCYCHa51 XOpOWO p B H,O
(6e3BOAHa5l- 70-80% - YKCYCH8f1 3CCeHLj/l1f1
neAHHa5l) 3-6% - 'YKCYC
A OCTOPO)KHO! np'" nonaAaH"'''' BO BHYTPb
opraH"'3Ma - C"'llbHble O>Kor",.
HCnOJlb3yenLcSL npll npUZOnWOJlenUu. nUUll. a 6btmy, npoMeJlcynw1l-
liblU npo{JYlcm (j OpZUUUlleClco..i1 Cllumese. IIpou36o{J1iblC ffUCJlO-
mbL - 6 C/X (zep6ulfuiJbL 2,4 iJuXJlOpgJeliOKcuYKCYCHLUI KLlCJtOma)
nanbMIIITIilHoBaSi C'5H 31 COOH mepAble,  B H 2 O
CTeaplilHOBaSi C 17 H 35 COOH HepaCTBop"'Mbl, CMeCb -
CTeapWH.
BXOA5IT B COCTaB >KWPOB.
HaTp",eBble con", K",cnOT - Mbino.
77

OTAenbHble npeACTaBMTenM
Kap6oHOBbiX KMCnOT
(npOAOn>KeHille)
CH 2 =CH-COOH>KMAKOCTb,  CMeWMBaeTC5I C H 2 O,
aKp"'llOBa51 CnMpTaM"', 3cP"'paMM ,
(npOneHOBa5l) HCXO{JllOC cbLpbe {JJliL np01l360{JCmea nOJllltepOe
K"'CllOTa (Op2CmeffJla, 1{aY1[Y1{OB lLOll1l006JJW1ilibLX CJJtQJl)
C 17 H 33 COOH MaCn5lHMCTa51 >K"'AKOCTb,
Olle"'HOBa51 HepaCTBOp"'Ma B H 2 0, paCTBOp"'Ma B
K"'CllOTa OpraH",yeCK"'X paCTBOpMTen5lX
(LI",c-"'30Mep) 0
'l
CH 3 -(CH 2 )7 -CH=CH-(CH 2 )7- C
. 'OH
Bxo{hlm (j cocmaa pacmUmeJtbliblX JlwceJt. HCnOJlb.JYlOm B
npoU3BO{)Cmee meXH-lllleC"KUX JltaceJl, lCpaCllmeJteU, naptjJ10iltepllU.
06na1OT ,qBOCTBeHHO cjJYHKl\lIIeH (_C'lO C=C)
50nee ClllnbHble 'feM npe,qenbHble 'OH' /' ,
OCOOH ApOMaTIII'feCKaH CnlllpTO-KIIICnOT3
npOM3BOAHbie - 3cPcPeKTMBHbie
, OH lleKapCTBeHHble npenapaTbl
Canll1u.LlInOSaSi aCnl1pl1H - >KapOnOHM>KalO[4ee,
(opTO-r"'APOKc",6eHsoi'iHaH) canon - >KellYAOHoe cpeACTBO
KLllcnOTa
0"" 'l0 ABYXOCHOBHaH KlIIcnOTa
C-C Kp"'CTanll",yeCKOe Be[4eCTBO,  p B H 2 O,
HO /' 'OH cn"'pmx, 3cP"'pax, T o ,=189,5"C, rMrpo-
w,aseJ1esas:i CKonMHa
KIt1CnOTa OAHa 113 caMblX CMRbHblX Kap6oHOBbiX KucnOT
ConH-OKcanaTbl
IIpo,f/8Jl.flem XllJJill'leC"KuC C60ucmBa ffap6oHD6blX ffllCJtonz
(acmynaem liaK oaHa, mal{ II (Jae lcup601CCUJlbllbte zpynnbl).
COOH ApOMaTIII'feCKaSi ,qBYXOCHOBH3S1 KlIIcnOTa
0 !IIcxoAHoe Cblpb6 AJl51 nOllyeHM5I CMHTeT"'-
yeCKoro BOllOKHa n3BcaH.
Tepe<jJTalleBa
COGH KIt1CnOTa
78

CnO>KHble 3cJ>IIIPbl
CnO>KHble ac!>lIIpbl - :3TO Be[4eCTBa, MMelO[4Me 06[4YIO
cPOpMyny "",0 , rAe R M R' yrneBoAOpOAHble
R-C
paAMKanbl. 'O-R'
(llpOll360aHble lWCJlOm, y ffOmOpblX amOM H ZuiJpOffcozpynnbl
3aMeUjeH 1lll paallffaJl)
nOnY'feHllle npM B3a"'MOAeL1CTBMM Kap6oHOBbiX KMCnOT
'" CnMpTOB - peaKIIISI aTeplllc!>IIIKalIIlII.
(OT nm. aether - acPMp)
..yO _ _ _ _ _ HzSO(K),r "",0 + H 2 O
R-C +H,-OR' . .. R-C
'PH : 'O-R'
KV1CJlOTa cnlllpT cnQ)f(Hbliii ScPlIIP
Tpe6yeTc5I oTroHKa acpMpa.
HOMeHKnaryp3 ",0
CH -C'"
3 'O-CH
3
CD KMCllOTa + Cn"'pT YKCYCHOMeT",nOBblL1
"ScP L1 p" acpMP
@ Ha3BaHMe paAMKana MeT"'llal\eTaT
(OT CnMp'ra) + KOpeHb
naT"'HCKOrO Ha3BaHM5I
KMCnOTbi + aT
@) cnMpT "acpMp" + KMcnOTa MeT",nOBblL1 acpMp
YKCYCHOi:i KMcnOTbl
cJ)1II3111'feCKlile CBOCTBa neTYMe >KMAKOCTM
(HeT "H" CB5I3ei:i), Mano paCTBOpMMbI B H 2 0, XOpO-
WMe paCTBopMTenM, 06mlAalOT npM5ITHbIM 3an3XOM.
3Q)L1p 3anax
JJzypaBbllH09mUJlOBblii pOMa apOMam lf6em06,
nponuoHoBo6ymuJlOBblU ananaca RZOiJ, (jJPYKm06
YUCycHou30aMUJt06blU ZPYULU
JJzypa6bll1WCf.lJlUJlO6btU 6UUlllll - uanuv,ue 6 UUX
Y"KcYC1l0aMUJlOBblU 6analiOB Cn03/CUbtx a(jJUp06
MaC.TlJlJ-wamUJlOBblU a6pU1WCOB
ll30BaJlepbJlnOBOamUJI06blU .fI6JlOff
79

XIIIMIf1"1eCKlf1e CBOMCTBa
CnO>KHbIX acl>lf1pOB
HaJU1YII18 nOJlSlpII130BaHHOrO aTOMa KII1CJlOpO,[\a
O aKTII1BII13111PY8T CBSl3b
C-O-R' 111 OHa Jl8rKO
R-C pa3pblBa8TCSI ,[\a)K8
'O-R' no,[\ ,[\8V1CTBII18M BO,[\bl.
PaCUfenl£eHue CI£O:JfCHb£X 3tjJUp06 npu oeiicm6UU
600b£ Ha3b£6aemCR ZUOPOl£U30M (OMb£l£eHueM).
3ma pemw,U.fl o6pamT-la pemw,uu amepupUlwu,UU.
B npillCYTCTBiIIiII eno"'iII peaKillSi Heo6paTMa.
(o6pa30BaH1I18 COJlIl1 Kap6oHoBoVi KII1CJlOTbl)
'lO rlt1APOJlII!3 'lO
CH -c + HOH 4 .. CH 3 -C + C 2 H s OH
3 'O-C 2 H s 3Tepll!q>t.1KaL.J.lIIS1 'OH
YKCYCHoaH1J10Bblill YKCYCHaSl STillnOBbl1li
3<P"P l<iI'CI10Ta cnVlpT
'lO 'lO
CH 3 -C + NaOH -- CH 3 -C + C 2 H s OH
'O-C 2 H s 'O-Na
YKCYCHoaU1J10BbJiII au.eTaT
3<P"P HaTplllS1
80

I >K.....pbl. KnaCC.....<t>.....KaI.".....H. nony...eH.....e I
(M.I1IeepeJtb - ZUOPOJtU3 JlCUpOe, H.a'l.. XIX e.,
M.BepmJto-pewawJ/. amepUipUlwlUU, 1854 z.)
o
II
CH 2 - 0 - C - R
[ 0
11
CH - 0 - C - R
I 
CH 0 C R
JKUpbt - CllO:J/Cltbte arpuPbt,
o6paa06altltbte 1JllulfepultOM
U 6btCmuMU (:J/CUpltbtMU)
Kap6olt06btMU KUCllomaMU.
- - -
2
. >KlI1pbl
/
>KII1BOTHble paCTII1TenbHble
TBepAble )l(I1AKl1e
( IIICKnlO4eHI1e (l1cKnlO4eHllle
pb1611ii1 )l(l1p) KOKOCOBoe Macno)
o6pa30BaHbi o6pa30BaHbi
npeAenbHblM HenpeAenbHblM
KI1CnOTaMI1 KI1CnOTaMI1
C'5 H 3,COOH- C 17 H 33 COOH-
nanbMI1TI1HOBaSl Onel1HOBaSl
C 17 H 35 COOH- C 17 H 29 COOH-
CTeapl1HOBaSl nl1HOneBaSl
Bce JlCUpbt Jtee'l.e eoDbl, e BoDe HepacmBopuJv/.bt, XOpOUlO pacmeo-
pUJv/.bt B OpeaHU'l.eClWX pacmBopumeJtSlx (DuxJtopamaHe, 6eH3uHe).
nonY'feHe  
CH _CrH------i=lO:-C-R I CH 2 -O-C-R,
2 I I 0 [ 0
[I I II II
CH - q-l + HO:- C - R" -.,» CH - 0 - C - R" +3H 2 0
I I I 0 I 0
q I II II
Crl 2 -  _ _ _ _ _ JiQ- C - R", CH 2 - 0 - C - R,,"
rnllJu.eplIJH Kap6oHOBbie KLllcnOTbl :>KlIJp
81

XMMMl.feCKMe CBOMCTBa >KMpOB
1. r..ilAPomil3 >KlilpOB (oMblneHltIe)
o
II
CH 2 - 0 - C - C 17 H 35
CH 2 - OH
I 0 I
II
CH - 0 - C - C 17 H 35 + 3H 2 0  3C 17 H 35 COOH +CH - OH
I 0 CTeap"HOBaH I
II K"cnOTa CH 2 - OH
CH 2 - 0 - C - C 17 H 35
TplllCTeaplt1H
rll1114eplt1H
OMbll1.eUUe npoucxoiJum ueo6pamuMo 6 npucymcm6uu
Ufel1.o'leii (o6pasyemc.fl. i?JlU/tepUH U COJlb [WCJlOmbl)
2.rIilAPlilpOBaHlile
o
II
CH 2 - 0 - C - C 17 H 33
I 0
II
CH- 0 - C - C 17 H 33
I 0
II
CH 2 - 0 - C - C 17 H 33
Tplt101lelllH
(>K"AK"i'i)
+ 3H 2
o
II
CH 2 - 0 - C - C 17 H 35
I 0
p! II
7 CH - 0 - C - C 17 H 35
I 0
II
CH 2 - 0 - C - C 17 H 35
Tplt1CTeaplllH
(TBePAbli'i)
HCnOJlbSYlOemC.fl. B npOUSBoacmBe Mapzapuua.
If{UPbl .R6Jl.fllOmC.R 6aJICHOil cocma6Hoil '-laCmblO
nU14u '-leJl06eKa U JlCU60mHblX.
POJlb :J/Cupa B Opi?aHUSMe - 3uepZemU'leCKaR..
82

Mblna
Mbma - 3TO COnl1, 06bllJHO HaTpl1eBble 11 Kanl1eBble,
BblCWI1X Kap6oHOBbiX KI1CnOT.
C 17 H 35 COONa C,sH 31 COOK
CTeapaT HaTpllJS1
nanbMt-1TaT KanMfI
HmpweBble conw - TBepAble }
KanweBble conw - >KWAKWe
xopOWO
paCTBopWMbl B H 2 0
nOnY'"leHllle
1. OMblJ1eH...,e .J,1POB
(rwp,ponH3 B npl1cYTcTBHWl..4enOlJw) 
\1 
CH 2 - 0 - C - C 17 H 35
CH, - OH
I 0 I
"
CH - 0 - C - C 17 H 35 + 3NaOH--+CH - OH +3C 17 H 35 COONa
I 0 I MblIlO
" CH,- OH
CH 2 - 0 - C - C 17 H 35 -
2. OKJ,1.cneHJ,1e napacpJ,1HoB. C p,anbHeiiiwJ,1M
p,eiiiCTBJ,1eM COp,bl Na 2 C0 3
kaJ
2CH 3 -(CH 2 )'4 -CH 2 tCH 2 -(CH 2 )'4 -CH 3 +502 =
//0
= 4CH3-(CH2)'4-C, +2H 2 0
OH
2C,sH3,COOH+Na2C03=2C,sH3,COONa+H20+C02
MblnO
/{JLJI BbliJeJleHUil MbtJta iJo6aBJt,RlOm p-p NaCl. MbtJtO
BcnJtbtBaem - x03Rucm6ennoe MblJtO.
MbtJtO o6JtaiJaem OC06blMU n06epxnocmno-aKmU61tbtMU
c6oucm6aMu (MoJOUfee iJeucm6ue).
B JlCeCmKOU BoiJe MOlOUJ,ee iJeiicmmu' C.lWOO('
2C 17 H 35 COO- +Ca 2 + =( C I7 H. 1 "COO) ,Cat
83

CMHTeTM"IeCKMe MOlOlltMe
CpeACTBa - CMC
.
"'''f
, a_, -_
. " " '> 11 " 41 '
:\!. .;.
J .'
. ...;.,,,,,' -- " f
LlPOSVS', g
CMC - anKl1ncynbcpaTbl -
HaTpl1eBble Conl1 MOHOScpl1pOB
cepHO.:1 KI1CnOTbl C BblCWI1MI1
Cnl1pTaMI1.
RO-S0 2 0Na, rAe R- npeAenbHbl.:1
yrneBOAOpoAHbl.:1 paAI1Kan
(OT 8 AO 18 aTOMOB yrnepoAa)
HO
'-
R-CH - O H+ SO -) R-CH -O-SO - O H+H 0
2 / 2 2 2 2
HO K"Cllb'i'i CllO)/(Hbl 3<)J"p
Cnlt1pTa It1 CepHOH KII1CnOTbl
R-CH 2 -0- S0 2 -OH+NaOH -7 R-CH 2 -0-S02 -ONa+H 2 0
 j
V
CMC
COXpWUlem M.07014ee iJeucm6ue 6 JlCeCmKOU
60iJe U 6 KUCJlblX paCm60paX.
84

I YrneBOAbl. COCTaB. KnacclII<!>1IIKau.IIISII
YrneBOAbl ami'! caxapa - Bell\eCTBa, COCTaB KOTOpblX
06bl4HO Bblpa)l(aeTC5J Q:JopMynoi1 C X (H 2 0)y, rAe x 11 y  3
c]J0P.lIWJlbHO .lIW:J/CHO pacc:mampU6amb lW/{;
coeOUHeHUJI. YZJlepooa c 6000U => ucmOpU'I,eCRU
C.lW:HCU6ZUeeCIl na36anue - yzne6oiJb.
/ rl1APOKCl1nbHble rpynnbl -OH
COCTaB MoneKyn + O
------. OCTaTKI1 anb,D,en-1,D,OB (-C( )
I1nl1 H
"-
KeTOHOB ( C=O )
/
/'" anb,D,eri'!AOCni'!pTbl
YrneBoAbl  I1nl1
------. KeTOHOCni'!pTbl
o"
\j
 "
H 2 0 '\
hv (CBeT)
CbOTOCI.1HTe3
xC0 2 +yH 2 0  C x (H 2 0)y+X0 2
B paCTeHI-15JX - AO 80% cyxoro BelL\eCTBa
B OpraHI13Me 4enOBeKa 1-1 )l(I-1BOTHbIX - AO 2%
B nl-1lL\e 4enOBeKa ...:70%
yrneBO,D,bl
MOHOCaXapl-1,D,bl ,D,l-1caxapl-1,D,bl nonl-1caXapl-1Abl
C 6 H ,2 0 6 - rnlOK03a C12H220,1 - caxap03a (C 6 H 1O O S )"- KpaXMan
8S

I
I
rnlOK03a. CTpOeHMe. 4>pYKT03a
C H 0 I " . PI1CTannI14eCKOe Bell\eCTBO,
'1:\, 'sv XOpOWO P B H 2 0, cOAep-
6 12 6 )l(I1TC5J B COKe BIi1HOrpaAa,
cnenblX Q:JPYKTax, B MeAe.
BWHorpa)J,HblC1 caxap
(OT rpe'f. glykus - Clla)J,Kwi1)
B paCTBope
o
c(
I H
H-C-OH
--. I --.
+-- HO-C-H +--
1
H-C-OH
I
H-C-OH
H OH H--OH H OH
a-cpopMa 34% allb)J,erM)J,Has:1 J3-cpopMa 64%
(llIllKmIJ4eCKas:l) cpopMa 2% (LJ,IIIKnMl.IeCKas:l)
Cyw,ecm6YlOm oiJHo6pe.!ft.eHHO U .M.ozym nepexoiJumb
iJpyz 6 iJpyza - .fl.6JleHUe maymoMempuu.
He UiJOMepbt. He .M.ozym 6btmb 6bliJe.neHbt 6
UHiJu6uiJya.nbHO./lt 6uiJe. 6ceziJa 6.M.eCme.
i'laoMep - CJ>PYKToaa (Q:JPYKTOBbli:1 caxap)
C 6 H 12 0 6
OH H
a-d-CPPYKT03a
-KeTOHOCnl1pT. COAep)l(Ii1TC5J B
nnop,ax, MeAe. Cnall\e rmOK03bl.
-
-
H H H OH H HOCH,
I I - I I I --+-
H-C-C-C-C-C-C-H_
I I I I II I
OHOHOH H OOH
d-<j)PYKT03a
(lllllHeallHafi ct>opMa)
86
OH H
P-d-<j)PYKTo3a

I rnlOK03a. XMMM"IeCKlI1e CBOMCTBa I
C",O
XI1MIII4eCKI1e cBoi1cTBa o6ycnoBneHbi -OH 11 - 'H
.Ki'il( MHOfoarOMtU;ii1 CfU1PT
1. PeaK4'"'SI 3Tep'"'<lmKa4'"''"'
CH,OH
Q
H+
H
+5CH,COOH 
OH
+5H,O
H
OH
H OCOCH,
2. C r'"'APOKC'"'AOM MeA'"' (II) 6e3 HarpeB.aHI151
C6H'206 + CU(OH)2 -- CI1HI1I1 (BaCl1nbKOBbll1) pacTBOp
nQ.aJ1bAr,",AHoi1 rpynne
I. Ka<ieCTBeHHble peaK4'"''"' (peaKL.\1111 OKI1CneHI151)
1) peaK4'"'SI n cepe 6pSlHoro 3epKana n
H H H OHH H H H OHH
I I I I lor I I I I I 0
H-C-C-C-C-C-C::: +Ag 0 . H-C-C-C-c-c-c::: +2Ag!
I I I I I H 2 NHOH I I I I I OH
OHOHOHH OH OHOHOHH OH
rIlIOKOHOBafi KlilcnOTa
2) C r'"'APOKC'"'AOM MeA'"' (II) npl-1 t"
H H H OHH H H H OHH
I I I I lor I I I I I 0
H-C-C-C-C-C-C::: +2Cu(OH),= H-C-C-C-C-C-C::: +2CuOH+H,O
IIIII H CIiIHIil i.1 IIIIIOH -
O HOHOHH OH OHOHOHH OH ><6mbl"
. r
2CuOHCu,O+H,O
K aCHbl'-1
II. PeaK4'"''"' BOCCTaHOBneH,",SI
H H H OHH H H H OHH H
I I I I I 0 Ni I I I I I I
H-C-C-C-C-C-C +H, . H-C-C-C-C-C-C-H
I I I I I H t I I I I I I
OHOHOHHOH OHOHOHHOHOH
fnlOK03a - anbAer'"'Aocn'"'pT cop6m
87

rnlOK03a.Oco6ble
CBOMCTBa. npMMeHeHMe
6pO>KeHMe rnlOK03bl
1. Cnl1pTOBOe (kat-<!:JepMeHTbl)
cPepMeHTbl
C 6 H 12 0 6 = 2C 2 H s OH + 2C0 2 i
2. MOnOlJHOKI1Cnoe
C H 0 2CH - CH - C O
6 12 6 = 3 I 'OH
OH
Mo.n04Ha51 KII1C1l0Ta
nonHoe OKMCneHMe B OpraHM3Me
cPepMeliTbl
C 6 H 12 0 6 + 60 2  6C0 2 + 6H 2 0 + Q
a
; j
 gSQ
"
8
o
3EPKAllO
B MeAI-I41-1He I 
Cblpbe B np0l13BOAcme BI1TaMI1Ha C, . C#l.
rlllOKOHaTa Ca, nl1TaTellbHoe B-B? 11 % fiJ
KOMnOHeHT KpOB03aMeHI1Tenel1 
(BHYTpI1BeHHble BllI1BaHI1)
B nl-lll.leBO" npOMblwnHHOCTI-I 
BXOAI1T B COCTaB HanI1TKOB, KOHAI1TepCKI1X
113Aell11M. Cop611T - 3aMeHI1Tellb caxapa ".,
All ,L\l1a6eTI1KOB, naTOKa. nonyeHl1e C,H,OH;
113roToBlleHI1e KI1CnOMOllOYHblX }
r ::' . KOH4JETA
npOAYKTOB (MonOHa KI1CllOTa) \/. _
B TeKCTl-lnbHO" npOMblwneHHOCTI-I
npl1 KpaWeH1111 11 annpeTI1BaHl111
(npl1AaHI1I1 611eCKa) TKaHeM 11 KO>KI1.
B npOl-l3BOACTBe 3epKan 1-1
enO'fHbiX I-IJ"pyweK
(cepe6peHl1e)
88

I CaXap03a. CTpOeHMe. CBOMCTBa I
I C H 0 I Kp"c,,,"""""c",,e ,e"1ecrno,
, 'sv xopowo P B H 2 0,
12 22 11 T nn =185"C, 60nee cnaAKoe,
4eM rmOK03a.
CBeKnOBI1'fHbIW 111111
TPOCTHI1KOBblW caxap
(06b1KHOBeHHbIW caxap)
1"
C'2H22011 + CU(OH)2 -7 CI1HI1M  HeT 1t13MeHeHIt1M
paCTBOp
t"
C'2H22011 + A9 2 0 
NH 4 0H
Caxap03a - MHoroaTOMHbl'" cn"'pT, HO He anbAenlA.
CH,OH CH,OH
Q 0
e
H
OH
OH
H
OCTaTOK rlllOK03bl
OCTaTOK CPPYI<TOSbl
MoneK}'na caxap03bl COCTOIliT 1113 coe,qIllHeHHbiX ,qpyr C
APyroM OCTaTKOB rmOK03bl III 4IPYKT03bl
OCHOBHoe CBOMCTBO - rl1APOnl13
C12H22011 + H 2 0 . C 6 H 12 0 6 + C 6 H 12 0 6
caxap03a rlllOK03a CPPYKTo3a
nplt1MeHeHlt1e -7 nonY4eHIt1e caxapa.
R9

nonMcaxapMAbl (C 6 H 1 oOs)n
npMpOAHble nOnMMepbl
COCTaB 11
cBoCicTBa
COCTaB
CrpYKTypa
MoneKyn
KpaXMan
Ll,enmono3a
(KneTLJaTKa)
(C 6 H1OOs)n
yrneBoAbl
nOnl1caxapli1Abl
npli1pOAHble nOnli1Mepbl
n,p=1000 I n,p«n"en
<
M,p
20%
1U1HeMHafl

80%
pa3BeT -
BneHHafi
Ml\eJ1

TOIlbKO nlllHeiltHafi
CrpYKrYPHoe
3BeHO
ct>1iI3I1LJeCKl1e
cBoCicTBa
HaXO)I(AeHl1e
B npl1poAe
H OH
6ellbiM XPYCHH.I1a-1W
flOPOWOK, B XOllOAHOW
BO,L\e H, B rop'few -
KOJlllOMAHblW paCTBOp
(KllewcTep)
B 3epHOBbiX (pMce -
80% - KYKYPY3e,
nWeHMl\e - 70%), B
KapTOcpelle - 20%.
06pa3yeTc B
pacTeHMx 3a ceT
cpOTocMHTe3a.
90
OCTaTOK
l3rIlIOKo3bl
H OH
TBepAblW BOJlOKHa-ICTbIW
MaTep, a-Iall B H,O a-I
APyrMx paCTBOpMTellx
H, npOYHblW
B xllonKe-98%, B
BOllOKHax llbHa,
KOHOnJlM, B ApeBeCMHe-
50%, B TpaBe, llMCTbX
AepeBbeB 10-25%.
"cKelleT" -060JlOKa
pacTMTellbHblx KJleTOK

KpaXMan M 4ennlOn03a
XMMlI1l.feCKMe CBOMCTBa
KpaXMan
Ll,enmono3a
1. rMAP?nM3
(C 6 H1QOs}n + nH 2 0 .::; nC 6 H 12 0 6
rnKJK03a
o6pa3yeTc a-rmOK03a
(1811r., K.C.Kl1pxro<jJ!
KpaXMall ---> AeKCTI1Hbl --->
---> ManbT03a ---> rmOK03a
2. Ka<ieCTBeHHaSi
c eaK lU 1S1
c paCTBOpOM iiioAa
KpaxMan+J 2  CI1Hee
OKpaWI1BaHl1e
KpaXMan-Ba)l(Hbliii npoAYKT
nl1TaHI151 4enOBeKa,
l\enmOn03a - HeT.
CPepMeHTbl 4enOBeKa,
cnoco6cTBYIOll\l1e
rl1APOnl13Y KpaXMana
He AeiiicTBYIOT Ha CB513b
Me>KAY OCTaTKaMI1
f3-rnIOK03bl.
Ll,ennlOno3a He
nepeBapI1BaeTC51.
o6pa3yeTc j3-rnIOKo3a
2. 06pa30BaHI1e cno)l(-
HblX 3<Pl1pOB C OpraHI1-
4eCKI1MI1 11 HeOpraHI1-
4eCKI1MI1 KIIICnOTaMI1.
C a30THOM KlilcnOToM
[C 6 H 7 0 2 (OH)3]n +3nHON0 2 
 [C 6 H 7 0 2 (ON0 2 )3]n +3nH 2 0
Tp"'H"'TpOl1elllllOllosa
(n"'pOKC"'ll"'H, 6eSAbIMHbli'i
nopox) BB
C YKCYCHOM KMcnOTOM
[C 6 H 7 0 2 (OCOCH 3 )3]n
Tpl1a4eTaT 4elllllOl103a =>
AJl nonY'feHI1 I1CKYCCT-
BeHHoro a4eTaTHoro BOllOKHa.
3. rOpeHl1e
(C 6 H IO 0 5 )n +02C02+H20+Q
4. 6e3 Aocryna B03Ayxa -
TepMI14eCKOe pa3no-
)l(eHl1e. 06pa3yeTC5J
CH 3 0H, CH 3 COOH,
(CHS)2CO 11 Ap.
91

AMIftHbl. COCTaB
HOMeHKnaTypa. M30MepiftH
AMI1Hbl - np0l13BOAHbie NH 3 , B MoneKyne KOTOpOro
aTOMbl BOAOpOAa yaCTI1YHO I1nl1 nOnHOCTblO 3aMell.\eHbi
yrneBoAopOAHblMI1 paAI1KanaMI1.
R - NH R 1 'NH R 1 'N - R
2 R --- R --- 3
2 2
nepBI1YHbl BTOpI1YHbl TpeTI1YHbl
Cl>yHK'-'MoHanbHaR rpynna - NH 2
paAI1Kan + -aMI1H
/ (B nOpS1AKe YBenl1yeHI1S1)
HOMeHKnaTypa 3TllfnaMllfH
CH,-CHz-NHz  COOTBeTCTBYIOIl.\I1 yrneBoAo-
POA C npI1CTaBKO aMI1HO-
aMllfH03TaH
I yrnepoAHOrO CKeneTa CH 3
1
CH - CH - CH - CH CH -C-CH
3 I 2 3 'I 3
H30MepMR NH 2 NH 2
 2-aMV1Ho6YTaH 2-aML1HO-2-Men11lnpOnaH
nOnO>KeHMR aMMHorpynnbl
CH, -CH z -CH 2 -CH 2 -NHz CH 3 -CH-CH 2 -CH 3
I
NH 2
1-aMt.1H06YTaH 2-aMII1Ho6yraH
Cl>M3M'IeCKlile CBOv.CTBa
npOCTeWl1e i C 3 NH, } XOPOWO
60nee CnO)l(Hbie - )I(I1AKOCTI1 C 3 pbl6bl P B H 2 O
BblCWl1e - TBepAble, ja, B H 2 0 He paCTBOpl1Mbl
92

I AMIftHbl. XIftMlft'"leCKlfte CBOMCTBa I
XIIIMlII"leCKllle CBOHCTBa o6ycnoBneHbl Hanlll"lllleM
HenOp,eneHHOH aneKTpOHHOH napbl a30Ta.
8- 8 8::
.. ..
NH 3 < RNH2 < R1NHR2
)
YBenW-jeHl1e sneKTpoHHoti nnOTHOCTI1 Ha aTOMe N
AMI1Hbl - OpraHWieCKlile OCHOBaHI1S1
(6onee Cl-1nbHbie, LJeM NH 3 ).
CBOVlCTBa CXOAHble C NH 3
1. PaCTBOp aMIiIHOB B BOAe IilMeeT l.1.Ienol.JttyIO peaK4lllIO
[ J +
CH 3 8+ CH 3
H-:H : OH  H-- H OH-
2. C KlilcnOTaMIiI
nllAPOKCIfIA Men.maMMOHIflf1
(clla60e OCHOBaH",e)
?H3 8+
H-N: '4=H : CI 
I
H
[ J +
CH 3
H--H cr
XIlOpLIIA Men11JaMMOHIt1
(COllb)
3. Oco6oe CBOiitCTBO - B OTnl1I.JI1e OT NH 3 ropHT Ha
B03Ayxe
4CH 3 - NH 2 + 90 2 = 4C0 2 + 10H 2 0 + 2N 2
nonYl.JeHlile BOCCTaHOBneHl1e HI1TpOCOeAI1HeHl1ti
CH 3 N0 2 + 3H 2
Pt.Pd,Ni
r ) CH 3 NH 2 + 2H 2 0
93

AHMnIllH.CTpoeHMe.CBOMCTBa
@-NH 2
ApoMaTWJeCKI1L;1 aMlIIH, B COCTaBe
KOTOpOro apOMaTW-/eCKlIIL;1 pa,lJ,I1Kan
cPeHlIIn CBH3aH C aMIi1HorpynnoL;1.
cPeHlllnaMa.1H
aHltlm<1H
MaCnHHlIICTaH )l(lII,lJ,KOCTb,,I«, 3, Ha B03,lJ,yxe >KenTeeT -
- OKI1CnHeTCH, nnoxo paCTBOpl1M B BOAe,
T,"o= 184,4°C, Ci'lnbHblVi SI,t:\.
 :NH2 p-n 3cPcPeKT COnpH>KeHlIIH p-3neKTpOHOB N 11
n - nnOTHOCTlII H,lJ,pa.
b- 0 b- NH 2 - ,lJ,OHOp e, OPTO-, napa- OpllleHTaHT (KaK
rl1,lJ,pOKcorpynna)
b YMeHbWeHl1e 3neKTpOHH0L;1 nnOTHOCTI1 Ha aTO-
- Me N CHI1>KaeT OCHOBHble CBoL;1cTBa aHlIInl1Ha.
NH,
@ < NH 3 < CH 3 -NH 2
Xi'lMi'I'IeCKi'le CBOVlCTBa
-NH 2
C KI1CnOTaMI1 (,lJ,OHOpHO-
aKlI,enTOpHblL;1 MeXaHI13M)
.B+ -+ _
C6H5NH2+HCI->[C6H5NH3] CI
xnoplllA <j)eHllln-
aMMOHIIIS1
( rlllAPOXnoplt1,lJ,
8HlflnlllHa)
@
C 6POMH0L;1 BO,lJ,oL;1
NH 2 NH 2
@ +3Br 2 -Jr-@-Brl+3HBr
Br
2,4,6-TpH6pOMaHW1It1H
(6e.nblitt !)
B3a"'MoAei1cTBli1e C ralloreHa-
M"',H"'TpOBaHli1e "'AeT ner'fe,
'feM y 6eH30na.
nonY'IeHi'le (1842 r peaKlI,l1H 3111HlIIHa) - BOCCTaHOBne-
Hl1e HI1Tpo6eH30na CepHI1CTblM aMMOHlIIeM
C 6 H 5 N0 2 + 6H --7 C 6 H 5 NH 2 + 2H 2 0
OCHOBHble CBOHCTB3 60nee
cna6ble, 'feM y aMMli1aKa.
94

AMMHOKIftCnOTbl. HOMeHKnaTypa.
M30MepiftSi
NH 2 -R-COOH
HOMeHKnaTypa
3 2ct 1
CH 3 - CH - COOH
I
NH 2
OpraHI14eCKII1e 611cPYHKlI,I10HanbHble
COeAII1HeHII1, B COCTaB KOTOpblX BXO-
Am ABe cPYHKlI,I10HanbHbie rpynnbl -
Kap6oKclIInbHa cgHlII aMlIIHO -NH.
C"CTeMaeCKaH paQ"OHanbHaH
YrllepoAHble aTOMbl
0603Ha4alOTcSI rpe-
eCK"'MII1 6YKBaM'"
a, P,y..., HaYII1HaSi C
aTOMa G, COeAl1HHe
Hom C -GOOH
rpynnoiii
KI1CnOTa C npl1( l-raBKot1 aM"HO-
2-aM"'HonponaHoBaSi a-aM"'HOnpOnIl10HOBaS
KII1CllOTa K"'CllOTa
nOllO>KeHlI1e aMII1HO-
rpynnbl YKa3blBaeTcSI
l\1I1<ppoiii
yrnepoAHoro CKeneTa CH 3
t CH -CH-CH -COOH CH -C-COOH
3 I 2 3 I
/ N N
/ 3-aMl.ilHo6yraHoBa51 KlltCJ10Ta 2-aMItIHO-2-MenmnponaHOS8s:!
KIt1CJ10Ta
30MePMH- \ ::;;,::::rp:8H_CH2_com
I I
NH 2 NH 2
a-aMIIIHOM8CllSn-iafi KII1CJ10T8 r3-aM[4HOMaCS1Hafi KlAC1l0Ta
KnaCCOB COeA"HeH" C n H 2n +,N0 2
(HI1TpOCOeAI1HeHI1)
4 :3 2. 1
CH 3 -CH 2 -CH-COOH CH 3 -CH 2 -CH 2 -CH 2 -N0 2
I
NH 2
2-aM1-1Ho6yraHOB8s:J KlllcnOTa l-Ha.1Tpo6yraH
95

AMIftHOKIftCnOTbl. CBOMCTBa
cJ>M3M"IeCKMe CBOMCTBa' TBep,L:\ble, j\..\, /3, cna,L:\-
Kille, XopOWO P B H,O, nplll r 250-300°C pa3naralOTc
XMMIII"IeCK Me CBOMCTBa
. (N H,- R - CO GH ---) NH,+- R - COO- (BHYTpeHH conb)
,L:\etlicTBllle Ha IIIH,L:\IIIKaTOpbl [H+]=[OH-] cpe.n,a HetliTpanbHa
AMI1HOKlllCnOTbl - aMcpOTepHble OpraHIII'feCKllle COe,!J,lllHeHIII
I.CBOMCTBa KMcnOTbl
1. C MeTannOM
2NH,CH,COOH + 2Na = 2NH,CH,COONa + H,!
2. C OKCIIIAOM MeTanna
2NH,CH,COOH -!- MgO = (NH,CH,COO),Mg + H,O
3. C OcHOBaH....eM
NH,CH,COOH + NaOH = NH,CH,COONa + H,O
4. C conblO
2NH,CH,COOH+ Na,C0 3 =2NH,CH,COONa +H,O+CO,!
5. PeaKLI....SI 3Tep....cI>....KaLl........ (co cn....pToM)
NH,CH,C :::\&B;O-C,Hs --> NH, -CH, -C ::: g-C,Hs +H,O
II.CBOMcTBa OCHOBaHIIIH
.(N H,CH,COOH + HcI ---) [HOOC-CH,--NH 3 r cf
III.B3aIllMOAeMCTBllle MoneKyn APyr C APyroM
(nonMKOHAeHca1..(MH) - 06pa30BaHI1e nenn-1AOB
H
NH-CH-C"'9--+HN-CH-C"'0 
, '....'.Q}::L) '....OH
[   -I   ",0
C-N NH,-CH,- C-N -CH,-C" +H,O
nenTIt1AHa51 rpynna I aMIt1AHafl CBfl3b OH
p,!'InenTW
96

I HeKOTOpble aMIllHOKIIICnOTbl 6enKOB I
Ha3BaHi'le
C!>opMyna no CIilCTeM3T111- no p3L\IIIOHanb- TpIllBIII-
'feCKO" HOMeH- HO" HOMeHKna- al1bHoe
KnaTYpe Type
-
H,N-CH,-COOH AM"'HOSTaHOBaH AM"'HOYKCYCHaH rll"'I1"'H
KIfIGnOTa H1cnOTa (m",)
CH,-CH-COOH 2-AM"'Honpona- a-AM"'Honpon",- a-AllaH"'H
I HOBa5I KL-1GnOTa OHosafi KIfICIlOTa (ana)
NH,
CH -CH-CH-COOH 2-AM"'Ho-3-Me- a-AM"HO"'SOBa- Ball"H
" 1 T"1l-6YTaHOSaH llepbHHOBaH (Ball)
CH, NH, KItICllOTa K"'CllOTB
C-CH-cH,-cH-COOH 2-AM"Ho-4-Me- a-AM"HO"SO- Jleiil1"'H
1 1 TI..1n-neHTaHQBafi KanpOHOBaH (118i'i)
CH, NH, KLllcnOTa KIfICIlOTa
CH,-CH,-CH-CH-cOOH 2-AM"'Ho-3-Me- a-AM"'Ho-p-Me- I1so11ei'i-
1 I n'1n-neHTaHOBafi TI / 1J1BanepbflHOBafl I1"'H
CH,NH, KlflcnOTa KlflcnOTa ("'llei1)
CH, -CH-CH-COOH 2-AM"'Ho-2-r"'A- a-AM"Ho-p-r"A- TpeOH"'H
1 1 pOKc",6YTaHOBaH pOKclfIMacnsmafl (Tpe)
OH NH, KlflcnOTa KIt1CnOTa
CH,-CH-COOH 2-AM"'HO-3- a-AM"'HO-- L\",cTe"'H
I I n'lOnpOnaHosafi TlflonpOillflOHOSas:l (I1"'C)
SH NH, KIfICnOlQ. KlflcnOTa
CH,-(CH,),- CH-COOH 2,6-A",aM"'HO- a,E-A",aM"'HO- Jhfl31f1H
I 1 reKcaHosafl KanpOHOBafl (11"'3)
NH, NH, KMGnOTa KLllcllOTa
HOOC-CH, -CH-COOH 2-AM"H06YTeH- a-AMIfIHOflHTap- Acnapa-
1 Alflosafl KlflcnOTa Has:! I<LIICnOTa rlfIHOB3f1
NH, KItICnOTa
(acn)
97

nonY'"leHlfte 1ft nplftMeHeHlfte
aM 1ft HOKIftCnOT
nonYLleHl1e
1.1.13 Kap6oHoBbiX KI1CnOT
CI, NH,
CH 3 - CH .COOH -Hd CH 3 -9H-COOH -Hd CH 3 -yH-COOH
aKTL1BlIJpOBaH CI NH.
2.fI1APOnI13 6enKoB
npl1MeHeHl1e
1.a-AMI1HOKI1CnOTbl Heo6xOAI1Mbi AnSI CiIIHTe3a
6enKOB B opraHiII3Me.
2.neKaCTBeHHble npenapaTbl
rnYTaMI1HOBa5J KI1CnOTa - npl1 HepBHblx 60ne3H5JX
rl1CTI1AI1H - npl1 5J3Be )l(enYAKa
3.npOill3BOACTBO CiIIHTeTW'leCKiIIX BonOKOH
E - aMI1HOKanpOHOBa5J KI1CnOTa  KanpOH
£ /) y 13 a H
?H2 --CH, --Cl{ --CH, --CH, --C g-i +N--CH, --CH, -CI{ --Cl{ --CH, -C  gH->
NH, l H --' ° ]
1 "
-> - N -(CH,),- C - n +nH,O
KanpOHOBoe BonOKHO
0)- aMI1H03HaHTOBa5J KI1CnOTa  3HaHT
----- H
1 I I
NH.-(CH')6-COOH+H-N-(CH')6COOH -7
L _ _ __I
-7 [-NH-(CH.)6-CO-]n+nH.O
3HaHT
98

6enKM. COCTaB. CTpOeHMe
(TeOpl1S1 3.CI>lIIwepa)
6enKI-1- CnO>KHble, BblCOKoMoneKynflpHble
npl-1pOAHble COeAI-1HeHI-1f1,
nOCTpOeHHble 1-13 (X- aMI-1HOKI-1CnOT
AMI-1HOKI-1CnOTbl B 6enKaX CBfl3aHbi nenTI-1AHblMI-1
CBfl3f1MI-1 ( 9  )
-c - N-
[! [ M
H H 0 -- H HO M H H 0
I I ,,'II I I 11 1 I 11
...- N - c- C - N - C - C - L C - C -...
I .- 1-  I
R R' R"
R,R' ,R", - 60KOBbie paAI1Kanbl 0AI1HaKOBbIX I1nl1
pa3nW-jHblX aMI1HOKI1CnOT.
OKono 20 Bi'I,QOB aMi'lHOKi'lCnOT BXO,QHT B COCTaB
6enKoB.
HaXOAs:lTCfI B npOTOnna3Me 1-1 flApe Bcex
paCTI-1TenbHblX 1-1 )/(I-1BOTHbIX KneTOK, flBnfllOTCs:I
rnaBHblMIll HOCIllTenSlMM >KM3HIII.
anb6YM"'H (B KyplllHOM 5111u,e)
reMorno611H (B KpOBIII 4enoBeKa)
6enr<OBa51 MoneKyna reMorno6111Ha -
(C738H'16602"S2Fe),
Ka3elllH (B KopOBbeM MonoKe)
MIIIorn06111H III MIII03111H (B MbIWU,ax)
")f(M3Hb eCTb cnoco6 cYUjecTBoB8HMR 6enKOBblX Ten"
(CP. 3HrenbC)
99

CTPYKTYPbl6enKa
5enOK - nOnlllnenTMA
1. nepBM"IHaSi
CTpYKTypa
nocneAOBaTenbHOCTb
aM 111 HOKlllcnOT
2. BTOpM"IHaSi CTpYK"rypa -
cnlllpanb j 3a CyeT
BOAOPOAHblX CBs:l3eiii
H
I"
:: C=O 111 :N.....
3. TpeTM"IHaSi KOHcplllrypalIIs:1  .
CTpYKTYpa cn 111 pan 111 JI
(B3alllMoAeiiicTBllle - NH 2 , -OH, -COOH rpynn,
He Y4aCTBYIOUJ,IIIX B nemlllAHoiii CBs:l3111)
Aeii1cTBl1e XI1Ml1yeCKI1X BeLllecTB
(KI1CnOT, LlIenoyeiil, Cnl1pTOB, al\eTOHa),
HarpeB AO BblCOKI1X r, AeiilcTBl1e
paAI1 al\11 11 , coneiil TS1)1(enblX MeTannOB
=> pa3pyweHI1e 2 11 3 CTPYKTYP -
AeHaTypa4i-1H.
100

XIftMlft'"leCKlfte CBOMCTBa 6el1KOB
6enOK IIIMeeT MHOro CPYHKlI,lIIHanbHblX rpynn,
OTHeCTIII K onpeAeneHHOMY Knaccy HeIlb3s:1 -
- BblCWaSi cS>OpMa pa3BMTMSI
OpraHW-IeCKMX BelJ.!,eCTB
1. nOA Aei1cTBl1eM KI1CnOT I1nl1 cpepMeHToB - niAponlll3
I I
0 ' H 0 I H
II I I II I I
I I
H 2 N - CH 2 - C T N - CH - C --r N - CH - COOH + H 2 0--7
tit I tit ]
HOH CH 2 HOH CH 2
I I
OH SH
,,0 ...,0
--7H N-CH -C '" +NH -CH-C '" +NH -CH-COOH
2 2 'OH 2 I 'OH 2 I
CH 2 CH 2
I I
OH SH
r"'APOll"'3 Tp",nenT"'Aa
Ka'ieCTBeHHble p eaK u lII1II
2. Pa3nO)l(eHI1e npl1 r - aanax )IOKeHbIX nepbeB
3. BeTHble peaK4i'1l11:
Kcanmonpomeun06aJ/.
NH.OH
p-p 6enKa + HN0 3 (KOHl\) --7)1(enTOe --7 OpaH)I(eBOe
OKpaWI1BaHl1e
6uypem06aJ/.
p-p 6enKa + CU(OH)2 --7 KpacHo- cpl10neTOBOe
OKpaWI1BaHl1e
101

......30MepMSI KnaCCOB COeAMHeHMM I
onecp!;1Hbl l\!;1KnO- anK!;1Hbl an KaA!;1eHbl
napacp!;1Hbl
"" / "" /
C n H 2n C n H 2n - 2
/ "" / ""
reKceH-1 l\!;1I(flOreKCaH 6YT!;1H-1 6YTaA!;1eH-1,2
Cn!;1pTbl npOCTble anbAer!;1Abl KeTOHbl
OAHoaTOMHble 3cp!;1pbl
"" / "" /
C n H 2n + 2 O C n H 2n O
/ "" / ""
3TaHon A!;1MeT!;1nOBbICi nponaHanb A!;1MeT!;1n-
3cp!;1p KeTOH
(al\eToH)
Kap6oHoBbie
K!;1CnOTbl cnQ)I(Hble aM!;1HO- H!;1TpOCOe-
(npeAenbHble) 3cp!;1pbl K!;1CnOTbl A!;1HeH!;1S1
"" / "" /
C n H 2n 0 2 CnH2n+1N02
/ "" / ""
6YTaHoBaS1 3T!;1nOBbICi aM!;1HO- H!;1Tp03TaH
K!;1CnOTa 3cp!;1p YKCYCHaS1
YKcyCHOCi K!;1CnOTa
K!;1cnOTbl
102

reHeTM'IeCKaSi CBSl3b
OpraHM'IeCKMX BeeCTB
 R-r R-OR, R C"'O
rallOreH- npOCTble - 'O-R
1
npO"'3BOAHble 3cP'" pbl CllO>KHble
3cPI.1Pbl
RIOH
Hr -Hr H,O H,O R,-OH
R-OH 0,
f H,O Cnl.1pTbl .L
I- H ,) C n H 2n H, CuO R C"'O
- 'OH
allKeHbI Kap6oHoBbie
u."'K11oallKaHbl R C"'O KI.1CllOTbl
- 'H Cu(OH), l'
allbAerL1,[\b rAg,O
r,
0,
I
C n H 2n + 2 r-R-c:::8H
allKaHbl ra11oreH3a-
Mew,eHHble
KI.1CnOTbl
H, -H, H,O
NH,
-2H C n H 21l _ 2 R-NH, NH,-R-C :::8H
 aJlK"'Hbl aM"'Hbl
allKaAl.1eHbl aMI.1HO-
K"'CllOTbl
TpI.1Mep- +H, nOJlKOHA
3aLtL1f1 cau,l.1S1
-4H C n H 2n _ 6 HONO, R-NO, (-NH-R-CO- ),
 apeHbl H"'Tpocoe- 6enKI.1
AI.1HeHI.1S1
eH-
R - yrllesoAopOAHblH paAIiIKaJl; r - raJlOreH
\03

Ka"leCTBeHHble peaKLI,MM
OpraHM"IeCKMX COeAMHeHMM
coe)J;HHeHHe 'peaKTHB Ha6JIIO)J;aeMaH
peaKn;H.II
AmWHbI 1) - 1) 06blHO ollpeAenlOTc
nyTeM "'CK11IO'-jeH"'
2) p-p KMnO, 2) He 06eC4Be'fIllB3eT
p-p KMnO,
3) n11aMS1 3) ropS1T ro11y60BaTblM
ll11aMeHeM
ArrKeHbI 1) 6poMHaH BOAa (Br,) 1) o6eC4Be'fIllB3Hllle
'"- '"
",C=C, pacTBopa
2) p-p KMnO, 2)o6eC4 B e'fIllB3Hllle
pacTBopa
<PeHOJI 1) 6poMHaS1 BOAa (Br,) 1) 06eCI1Be"'BaH"'e,
Bbllla,L\eH"'e OCaAKa
Tp",6poMcPeHolla
2) p-p FeC!' (XJ1Op"'Aa 2) Kop"''-jHeBo-cP",olleTOBblL1
>Kene3a III) p-p C 3anaXOM TYw",
(KpacK"')
Clm:pTbI 1) Na 1) BblAelleH"'e BOAopOAa (i)
2) p-p NaOH 2) He pear"'pyeT
3) ropeH"'e 3) ropm CBeTnbIM,
ro11y60BaTblM nllaMeHeM
MHoroaToM- Bac"'nbKOBblL1 .p-p -
Hbre crmpThI Cu(OH), 06pa30BaH"'e rll"'l1epaTOB
(rm.m;eprrH)
AJIb,ZJ;errr,ZJ;bI 1) Ag,O aMM"'aHblL1 1) peaKI1"' "cepe6pS1Horo
p-p, 1" 3epKalla" (Ag!)
2) Cu(OH)" 1" 2) "'3MeHeH"'e oKpacK'"
Cu(OH), --7 CuOH --7 Cu,O
CI/IHV1t1 )f(enTbl!i1 KpacHbliii
104

Ka"leCTBeHHble peaKLI,MM
OpraHM"IeCKMX COeAMHeHMM
(npOAOn>KeHMe)
coep;HHeHHe peaETHB Ha6mop;aeMa.1I
peaEn;HH
Kap6oHOBble \I1H,!\"'KaTOpbl: B paCTBOpe - K",cnaH Cpe,L\a
EHCJIOTbI 1) M-O (MeT"'nOpaH>K) 1) p030BblL;;
2) 11aKMYc 2) KPaCHblL;;
! MypaBb"'HaH - peaKl.\I.1H
"cepe6pS1Hora 3epKalla"
! one"'HOBaH - 06eCI1Be'f"'-
BaHl.1e Br, BOAbl '"
p-pa KMnO.
1) Cu(OH), 6e3 1" 1) Bac",nbKoBblL;; p-p
r JIlOEOaa 2) Cu(OH), np'" 1" 2) "'3MeHeH",e oKpacK'"
Cu(OH),  CuOH  Cu,O
CIIIHllliI1 >t<enTbl'-1 KpacHblil1
KpaXMaJI p-p ",oAa J, C"'Hee oKpaw"'BaH",e
AMIIHbI \I1HJJ.i'1KaTOpbl: B pacTBope - Ll1ellOHaH
cpeAa
1) llaKMyc 1) c"'H",L;;
2) M-O (MemllOpBH>K) 2) >KemblL;;
3) <jJ-<jJ (<jJeHoll!j:na11e"'H) 3) Ma11"'HoBbli'i
AHIIJIIIH 1) p-p CaOCb 1) "epHbli'i aH",n"'H"
(x11opHaH "'3BecTb) 2)06ecI1BeI.1BaH"'e,
2) 6poMHaH BOAa Bblna,L\eHl.1e 6enora OCa,L\-
Ka Tp",6pOM-aHI.111"'Ha (.J.)
l) HN0 3 (KOHL\.) 1) >Ke11TOe oKpaw"'BaH",e
BeJIoE 2) Cu(OH), 6e3 1" 2) KpacHo-<jJ"'ol1eTOBoe
oKpaw"'BaH",e
105

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WW
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D::!:
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:r  o
s:  rJJ. 
E:t' JJ'">    0 ;;; '"
o
:s:
11.
W
I:

---

5'-'
-

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g:
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=

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107

COAep>KaHllle
I. TeoplllSi XI1MIII'feCKOro CTpOeHIIISI Opr3HIII'feCKIIIX coe,qIllHeHIIIH
1 B03H"KHoBeH",e opraH"ecKoi'i X"M"''' KaK Haw", (1807r.
C1.6epl1 e ll"YC) . ................................................................. .............. 3
2. BeLl1eCTBa opraH"ecK"e " HeopraH"'ecK"e. CeCTBB " HeKO-
Topble cBoi'iCTBa oprBH"'ecK"x BeLl1eCTB ........................................4
3. AOCTPYKT"BHble TeOp,,"'................................................................... 5
4. CB513b nOHfln1H TeOp1.1111 XItIMI/Il.JeCKOro CTpOeHII1f1................................ 6
5. npe,L\nOCbl11K" BOSH"'KHOBeH"'H TeOP"'" X"M"'ecKoro CTpoe-
H"'H opraH"'8cK"X BeLl1eCTB ............................................................ 7
6. Teop"'H X"'M"'ecKoro cTpoeH"'H. OCHoBHble n0110>KeH"'H (1,2)............ 8
7. Teop"H X"M"8cKoro cTpoeH"H. OCHoBHble nOllO>KeH"'H (3,4)............9
8. Teop"'H X"M"ecKoro cTpoeH"R OCHoBHble n0110>KeH"' (5)............. 10
9. AllroP"TM nO"CKa BOSMO>KHbIX "soMepoB allKaHOB ("'SOM8p"'H
yrllepOAHoro CKelleTB) .................................................................. 11
1 O. Kllaoc",<jJ"KBI1" X"'M"ecK"" coeA"HeH"i'i, mn"'HbIX AflH op-
raH"eCK"X COe,L\"HeH"'i'i (no T"ny X"'M"eCK"X npeBpaLl1eH"i'i).........12
11. KnaCCII1<pII1KaLJ,lI1f1 XII1MI/ILJeCKII1X coe.o.II1HeHII1H, TlI1m,1LJHbIX ,[I,llfl
opraH"ecK"x C08A"HeH"i'i (no T"'ny paspblBa CBS") ....................13
12. Kllacc"<jJ"'Kal1"H ymeBOAopoAOB.................................................. 14
II. npe,qenbHble yrneBo,qopo,qbl
1. MeTBH. <1''''s'''ecK''e cBoi'icTBa. CTp08H"e MOlleKynbl...................... 15
2. sp3- r ",6p"'T"Sal1"'H ......................................................................... 16
3. AllKaHbl ......... ...... ..... ..................................................................... 17
4. I1soMepbl '" roMollor".................................................................... 18
5. AllKaHbl (HepaSBeTB11eHHoro cTpoeH"') " a11Kl<1J1bl ........................... 19
6. HOM8HK11BTypa (p a l1"OHallbHaH) ..................................................... 20
7. HOMeHK11aTypa (c"CTeMaT"'ecK)................................................. 21
8. Onpe.o.eneHII18 KayeCTSeHHoro CQCT2Ba OpraHItIl.jeCKItIX
COe,L\"HeH"i'i ........ .................................................................. ....... 22
9. X"M"ecK"'e cBoi'icTBa a11KaHOB ..................................................... 23
10. nOllyeH"e allKaHoB..................................................................... 24
11. np"'MeHeH",e a11KaHoB.....................................................,............ 25
12. W"K11oa11KaHbl (l1"'KllOnapa<jJ"Hbl, Ha<jJTeHbl) .................................. 26
III. Henpe,qenbHble yrneBo,qOpO,qbl
1. 3TI<1J1eH (STeH). CTpoeH",e MOlleKYllbl. sp2- r ,,6p"T"'3al1"'H ................ 27
2. AllKeHbl (olle<jJ"Hbl, ST"lleHOBble ym8BOAopOAbI) ............................ 28 '
3. CBoi'iCTBa MKeHoB................................ H ....................................... 29
4. CBoi'icTBa a11KeHoB..................................................... ...................30
5. np"'MeHeH",e a11KeHoB.................................................................... 31
6. nOllyyeH",e MKeHoB....................................................................... 32
7. A"eHoBble ymeBO,L\opoAbl (a11KB.L\"'eHbl).......................................... 33
108
8 X"'M"ecK"e cBoi'iCTBa a11Ka,L\"'eHOB (c COnpH>KeHHbIM" CBHSH-
. M"') nOllyeH"'e............................................................................. 34
9. 06Ll1aH XapaKT8p"'CT"'Ka KaYYKoB. I1x CTpoeH"e " cBoL;1CTBa........... 35
10. Al1eTl<1J1eH (STI<1H). CTpoeH"'e M01l8KYllbi sp-r",6pl<1T"'sal1" ............. 36
11. CpaBHeH"e cTpoeH"H c011eKYllbl STBHa, smlleHa '" al1eTl<1J1e-
Ha. CpaBHeH"'e CJ '" 1t cBHsei'i ......................................................... 37
12. AllK"'Hbl (al1eTl<1J1eHOBbl8 ymeBoAopoAbl)....................................... 38
13. X"M"'ecK"e cBoi'iCTBa a11K"'HOB ................................................... 39
14. X"M"'ecK"'e cBoi'iCTBa allK"'HOB ................................................... 40
15. np"'MeHeH"e BI.1eT"'118Ha.......:......................................................;
16. nOllyeH"'e al1em1l8Ha" era 10MOlloraB.......................................
IV. ApOM3TIII'feCKlile yrneBo,qopo,qbl
1. 6eHsoll. <1'''s''ecK'''e cBoi'icTBa. <1'opMY11a K8Kylle.......................... 43
2. SlleKTpoHHoe cTpoeH"'e 6eHsolla................................................... 44
3. X"'MIo1ecKIo1e cBoi'icTBa 6eHsolla .....................................................45
4. X"'M"8cK"e cBoi'iCTBa 6eHsolla..................................................... 46
5. ApeHbl (ApoMam8cK"'e ymeBoAopoAbl. AllK"'1l6eH3011bl) ................ 47
6. TOllYOll. X"'M"ecK"e cBoi'icTBa. Bsa"MH08 Bll"'HH",e aTOMOB B 8
M011eKYlle TOllyolla........................................................................ 4
7. npaB"lla Op"eHTBI1"" B 6eHso11bHOM K011bl1e.................................. 49
8. np"MeHeH"e 6eHsolla. n011yeH"'e apeHoB..................................... 50
9. CT"pOll. Ha<jJTe11lo1H. AHTpal1eH ....................................................... 5
10. reHeT"eCKaH CBHSb Me>KAY rpynnaM'" ymeBoAopoAOB ................. 53
11. 06Ll1"e CBe,L\eH"H 0 rpynnax ymeBoAopoAOB................................ 5
12. 06Ll1"e CBeAeH"'H 0 rpynnax ymeBoAopoAOB................................ 54
V. CnlllpTbl1ll cpeHonbl 5
1. npe,L\ellbHble oAHoaTOMHbie cn"pTbl ............................................... 56
2. X"M"eCK"e cBoi'icTBa cn"'pTOB ..................................................... 5
3. 3TaHoll (3TI<1J10Bbli'i cn"'pT)............................................................. 57
4. np"MeHeH",e np€,!\ellbHblx OAHOaTOMHblX cn"pToB .......................... 5
5. Cnoc06bl nOllyYeH" cn"pToB ........................................................5 0
6. npeAe11bHble MHoroaTOMHbie CO"PTbl .............................................6 1
7 npOCTble S<jJ"'Pbl ............................ 6
8: <1'eHollbl........... .:::::: ::: :::: ::::: ::::: ::: :::: ::: ::: ::: ::::::: ::............................ 62
9. X"'M"ecK"e cBoi'icTBa <jJeHolla (no r"'ApOKcorpynne) ..................... 63
10. X"'M"'eCK"8 cBoL;1CTBa <jJeHolla (no 6eHsollbHOMY K011bI1Y) ............64
VI. Anb,qerlll,qbl III K3p6oHOBbie KlIIcnOTbl
1. AllbAer"Abl. CTp08H"'e. HOMeHKYllaTypa. I1soMep"'H........................ 65
2. <1'opMa11b,L\er"'A. n011yeH"'e. CBoi'iCTBa .......................................... 6
3. CBoi'icTBa allb,L\er"'AOB ................................................................... 6
4 CBoi'iCTBa a11b,L\er"'AOB .................................................6U
5: KeToHbl ... .................. :::: :::: :::::: ::::................................................. g
6. n011yeH"e MbAer"AOB 101 KeTOHOB.................................................
7. Kap60HoBbie K"CllOTbl. rOMOllOrl1ecK"'i'i PHA.................................. 71
109

e. HeKOTOpble np€,!\811bHbI8 OAHOOCHOBHble K"'C110Tbl ..........................72
9. Kap60HQBbie K"'C110Tbl. CBoi'iCTBa ...................................................73
1 O. X"M"ecK"e cBoi'icTBa npeAellbHblx OAHOOCHOBHblX Kap6o-
HOBblX KlI1cnOT ............................................................................... 74
11.X"M"ecK"e cBoi'iCTBa npeA8l1bHbiX O.L\HOOCHOBHbIX Kap60Ho-
BblX KltIcnOT. ......... .... .... ..... ... ....... ...... ... ........ .._ ........... ...... ........ ..... -'5
12.nollyeH"e Kap6oHoBbiX K"CllOT .................................................... 76
13.0TAellbHble npeACTaB"Tell" Kap60HoBbiX K"CllOT. Kllacc,,<p"'-
KBI.1" .................. ................... ................................... .............m... 77
14. OTAellbHble npeACTBB"Tell" Kap6oHoBbiX K"CllOT. ......................... 78
VII. CnO>KHble 3c!nllpbl. >Klllpbl
1. CllO>KHble S<P"Pbl........................................................................... 79
2. X"M"ecK"e cBoi'iCTBa CllO>KHbIX S<P"pOB........................................ 80
3. )I("Pbl. Kllacc"<p"Kal1"' nOllyYeH"'e............................................... 81
4. X"M"ecK"e cBoi'iCTBa >K"POB ........................................................ 82
5. Mbilla ................... ........ .............................................. ................... 83
6. C"HTeTl1eCK"e MOIOLl1",e CpeACTBa (CMC) ..................................... 84
VIII. YrneBo,qopO,qbl
1. YmeBOAbl. COCTaB. Kllacc"<P"Kal1"............................................... 85
2. rlllOKoaa. CTpoeH"e. <1'pyKTOaa................................H.................... 86
3. rlllOKoaa X"M"eCK"e cBoi'iCTBa.................................................... 87
4. rlllOKoaa. Oc06ble cBoi'iCTBa. np"MeHeH"e..................................... 88
5. Caxaposa. CTpoeH"e. CBoi'icTBa .................................................... 89
6. n011"caxap"Abl (CoH 1O O S )n. np"p0.L\Hble nOll"Mepbl......................... 90
7. KpaxMall " l1elllllOlloaa. X"M"'ecK"'e cBoi'iCTBa............................... 91
IX. AMIIIHbl. AMIliHoKlllcnoTbl. 5enKlil
1. AM"Hbl. COCTeB. HOMeHKllaTYpa. l1aoMep".................................... 92
2. AM"Hbl. X"M"ecK"e cBoi'iCTBa....................................................... 93
3. AH"ll"H. CTpoeH"e. CBoi'icTBa........................................................ 94
4. AM"HOK"CllOTbl. HOMeHKllaTYpa. l1aoMep", .................................... 95
5. AM"HOK"'CllOTbl. CBoi'iCTBa .............................................................96
6. HeKoTopble aM"HOK"'CllOTbl 6ellKoB ................................................ 97
7. nOllyeH"e" np"MeHeH"e aM"HOK"C110T........................................ 98
8. 6ellK". COCTBB. CTpoeH"e ............................................................. 99
9. CTPYKTYPbl 6e11Ka ........................................................................100
10. X"M"ecK"e cBoi'icTBa 6e11KoB ................................................... 101
11. l1aoMep"H KllaCCOB coeA"HeH"i'i ................................................ 102
12. reHen1LJeCK25I CB513b OpraHItI'-jeCKItIX Bew.eCTB ..............................103
X. nplllnO>KeHllle
1. KaecTBeHHble peaKI1"" opraH"ecK"x coeA"HeH"i'i .....................104
2. KaecTBeHHble peaKI1"" opraH"eCK"X coeA"HeH"i'i ..................... 105
3. nep"oA"ecKaH c"CTeMa x"M"ecK"'x SlleMeHTOB ........................ 106
4. YCllOBHbl8 060aHaeH"H............................................................... 107
110