XII klasi

giuli andronikaSvili
mzia mamiaSvili
dali gulaia
qimia
XII klasi
Tbilisi
2010
gamomcemloba `klio~
aRmaSeneblis gamz.# 191, Tbilisi, saqarTvelo
tel.: (+995 32) 34 04 30; 899 50 33 76
Sinaarsi
Sesavali................................................................................................................................................................5
organuli qimiis sagani........................................................................................................................................5
I Tavi. organul naerTTa qimiuri aRnagobis Teoria. eleqtronuli Teoria............ 8
§1 organuli naerTebis aRnagobis Teoria....................................................................................................8
§2 eleqtronuli Rrublebis hibridizacia organul naerTebSi.........................................................10
§3 naxSirbadis atomTa Taviseburebani........................................................................................................13
§4 kovalenturi bmis gawyveta.........................................................................................................................15
§5 izomeria............................................................................................................................................................16
§6 organul naerTTa klasifikacia...............................................................................................................18
II Tavi. naxSirwyalbadebi.........................................................................................................................20
najeri naxSirwyalbadebi (alkanebi).............................................................................................................. 20
§7 alkanebis homologiuri rigi.....................................................................................................................20
§8 izomeria da nomenklatura.........................................................................................................................21
§9 eleqtronuli da sivrciTi aRnagoba.......................................................................................................24
§10 miReba...............................................................................................................................................................25
§11 alkanebis Tvisebebi.....................................................................................................................................26
§12 gamoyeneba.......................................................................................................................................................30
ujeri naxSirwyalbadebi................................................................................................................................33
§13 alkenebi. homologiuri rigi....................................................................................................................33
§14 nomenklatura. izomeria............................................................................................................................34
§15 alkenebis eleqtronuli aRnagoba.........................................................................................................36
§16 alkenebis miReba...........................................................................................................................................37
§17 alkenebis Tvisebebi.....................................................................................................................................38
§18 alkenebis gamoyeneba...................................................................................................................................41
§19 alkinebi..........................................................................................................................................................42
§20 acetileni.......................................................................................................................................................43
§20.1 miReba............................................................................................................................................................43
§20.2 acetilenis Tvisebebi..............................................................................................................................44
§20.3 gamoyeneba....................................................................................................................................................46
aromatuli naxSirwyalbadebi (arenebi)....................................................................................................47
§21 benzolis aRnagoba......................................................................................................................................47
§22 izomeria, nomenklatura............................................................................................................................49
§23 miReba...............................................................................................................................................................50
§24 benzolis Tvisebebi.....................................................................................................................................50
§25 atomTa urTierTgavlena toluolis magaliTze...............................................................................52
III Tavi. JangbadSemcveli organuli naerTebi.............................................................................55
naxSirwyalbadebis hidroqsinawarmebi.....................................................................................................55
§26 najeri erTatomiani spirtebi (alkanolebi)........................................................................................... 56
§27 alkanolebis miReba.....................................................................................................................................57
§28 alkanolebis Tvisebebi...............................................................................................................................58
§29 gamoyeneba.......................................................................................................................................................62
§30 mravalatomiani spirtebi..........................................................................................................................63
§31 fenoli............................................................................................................................................................66
karboniluri naerTebi...................................................................................................................................69
§32 aldehidebi.....................................................................................................................................................69
§32.1 eleqtronuli aRnagoba..........................................................................................................................70
§32.2 nomenklatura. izomeria.........................................................................................................................70
§32.3 miReba............................................................................................................................................................71
§32.4 Tvisebebi.....................................................................................................................................................72
§32.5 gamoyeneba....................................................................................................................................................74
§33 ketonebi..........................................................................................................................................................75
§33.1 acetoni........................................................................................................................................................76
§34 karbonmJavebi................................................................................................................................................77
§34.1 miReba............................................................................................................................................................78
§34.2 karbonmJavebis Tvisebebi.......................................................................................................................79
§35 erTfuZiani karbonmJavebis warmomadgenlebi....................................................................................82
§36 esterebi..........................................................................................................................................................85
§37 cximebi.............................................................................................................................................................88
naxSirwylebi.......................................................................................................................................................91
§38 monosaqaridebi.............................................................................................................................................91
§39 disaqaridebi.................................................................................................................................................95
§40 polisaqaridebi. saxamebeli.....................................................................................................................97
§41 celuloza......................................................................................................................................................99
IV Tavi.azotSemcveli organuli naerTebi.................................................................................103
§42 aminebi............................................................................................................................................................103
§42.1 najeri aminebi..........................................................................................................................................104
§42.2 anilini.......................................................................................................................................................105
§43 aminomJavebi.................................................................................................................................................108
§44 cilebi...........................................................................................................................................................111
V Tavi. maRalmolekuluri nivTierebebi......................................................................................115
§45 polimeris sinTezi....................................................................................................................................115
§46 plastmasebi.................................................................................................................................................119
§47 xelovnuri da sinTezuri boWko............................................................................................................120
saxelmZRvaneloTi muSaobisas gaiTvaliswineT:
mocemuli davalebebi sruldeba gakveTilze rveulSi jgufurad,
wyvilebSi an individualurad, maswavleblis SexedulobiT .
saSinao davaleba
saSinao davalebebi.

davalebebi, romlebic sruldeba rveulSi gakveTilis msvlelobis procesSi an
damoukideblad saxlSi.
●
mocemulia informaciuli masala.
eqsperimenti.
Sesavali
organuli qimiis sagani
nivTierebaTa klasifikaciis pirveli cda iyo maTi dayofa
mineralur, mcenareul da cxovelur nivTierebebad.
nivTiereba
mineraluri
mcenareuli
cxoveluri
es klasifikacia daaxloebiT Mmravali saukunis ganmavlo­
baSi ucvleli rCeboda.
XVIII saukunis meore naxevridan daiwyo mcenareuli da
cxoveluri warmoSobis nivTierebebis intensiuri Seswavla.
eqsperimentis safuZvelze dadginda, rom yvela am nivTiere­bis Sedgeniloba erTnairia, isini Seicaven naxSirbads,
wyalbadsa da Jangbads. zogierT maTganSi gvxvdeba, agreTve,
azoti da fosfori.
XIX saukunis dasawyisSi Seiqmna mcenareul da cxovelur
nivTierebaTa calke Seswavlis aucilebloba. 1807 wels
Svedma qimikosma i. berceliusma wamoayena winadadeba, rom
cocxali organizmebidan miRebuli nivTierebebisaTvis
ewodebinaT organuli nivTierebebi, xolo maTi Semswavleli
mecnierebisaTvis _ organuli qimia. i. berceliusi Tvlida,
rom organul bunebaSi moqmedebs sxva Zalebi, vidre
araorganulSi, organul naerTTa miReba SeuZlebelia
laboratoriuli gziT, isini warmoiqmnebian mxolod cocxal
organizmebSi gansakuTrebuli `sasicocxlo Zalis~ (laT.
vis vitalis) gavleniT. i. berceliuss bevri mimdevari gamouCnda
Tanamedrove mecnierTa Soris da qimiaSi gamefda moZRvreba
`sasicocxlo Zalis~ Sesaxeb, anu vitalisturi Teoria.
miuxedavad imisa, rom vitalisturi Teoria amuxruWebda
organuli qimiis ganviTarebas, TandaTan grovdeboda did­
Zali eqsperimentuli masala organul naerTTa Sedgenilo­bisa da Tvisebebis Sesaxeb. XIX saukunis ocian wlebSi
germanelma qimikosma, i. berceliusis moswavlem f. violerma
araorganuli nivTierebebidan daasinTeza jer mJaunmJava
(gvxvdeba mce­nareebSi), xolo Semdeg Sardovana (warmoiqmneba adamianisa da cxovelis organizmSi). violeris am
aRmoCenebs mohyva organuli sinTezebis mTeli seria. 1845
wels germanelma qimikosma a.kolbem sinTezuri gziT miiRo
ZmarmJava. 1894 wels frangma qimikosma p. bertlom daasinTeza
cximebi, xolo 1861 wels rusma qimikosma a. butlerovma _
naxSirwylebi.
iens iakob
berceliusi
1779-1848
5
sinTezebis am jaWvma mTlianad gaacamtvera warmodgenebi
e.w. `sasicocxlo Zalis~ Sesaxeb da Seqmna safuZveli axali
mecnieruli Teoriis Sesaqmnelad.
1851 wels germanelma qimikosma a. kekulem organuli
qimia gansazRvra, rogorc naxSirbadis naerTTa qimia. aseTi
ganmarteba srulyofili araa, radgan naxSirbadis Sem­
cveli mravali naerTi (naxSirmJava, naxSirbadis oqsidebi,
karbonatebi da sxv.) miekuTvneba araorganul naerTTa klass,
radgan avlens araorganuli naerTebisaTvis damaxasiaTebel
Tvisebebs.
mogvianebiT organul qimias naxSirwyalbadebisa da
maTi nawarmebis qimia uwodes. miuxedavad imisa, rom nax­
Sirwyalbadebis TandaTanobiTi gardaqmniT SeiZleba miviRoT
TiTqmis yvela organuli nivTiereba, arc es ganmartebaa
srulyofili.
dReisaTvis gamoiyeneba rogorc erTi, ise meore gan­mar­
teba.
amrigad: organuli qimia Seiswavlis naxSirbadis Semcvel
naerTebs _ naxSirwyalbadebsa da maT nawarmebs.
organul naerTTa ricxvi amJamad 20 milions aRwevs, maSin
roca araorganuli naerTebis raodenoba naxevar milions ar
aRemateba. es imiTaa gamowveuli, rom sxva elementebisagan
gansxvavebiT, naxSirbadis atomebi mtkice bmebs amyarebs ara
marto sxva elementis atomebTan,
aramed erTmaneTTanac grZeli jaW­
vebisa da ciklebis warmoqmniT. garda
amisa, naxSirbadatomebs aqvs unari,
daukavSirdes rogorc erT­maneTs,
ise sxva elementis atomebs jeradi
(ormagi da sammagi) bmebiT.
organuli qimia axalgazrda mecnierebaa, radgan
igi Camoyalibda XIX saukuneSi. Tumca is SeiZleba
CaiTvalos uZveles mecnierebad, radgan organul
nivTierebebs da maT gardaqmnebs adamiani uxsovari
droidan icnobda da iyenebda: yurZnis wvenidan
Rebulobdnen Rvinos, marcvleulidan _ luds, mce­
nareebidan gamoyofdnen bunebriv saRebrebs, eTer­
zeTebs, cximebs, samkurnalo saSualebebs da sxv.
6
araorganuli naerTebisagan gansxvavebiT, organul naer­
TebSi atomebs Soris, ZiriTadad, kovalenturi bmebia.
amitom isini araeleqtrolitebs warmoadgenen da Znelad
urTierTqmedeben erTmaneTTan, aqvT dabali lRobisa da
duRilis temperaturebi, 600°C temperaturamde gaxurebisas
iSlebian. araorganuli naerTebis umravlesobisagan gan­
sxvavebiT, maTTvis damaxasiaTebelia izomeriis movlena.
organuli qimia aris safuZveli mrewvelobis mravali
dargisa, rogoricaa: saTbobis, saRebrebis, asafeTqebeli
nivTierebebis, sinTezuri kauCukis, qimiuri boWkoebis,
plastmasebis, organuli sasuqebis, Sxamqimikatebis, vita­
minebisa da samkurnalo preparatebis warmoeba.
gansakuTrebuli mniSvneloba aqvs organul qimias bio­
logiisa da medicinisaTvis. nebismieri cocxali arseba,
ZiriTadad, organuli naerTebisagan Sedgeba da nivTierebaTa
cvla, romelic safuZvlad udevs sasicocxlo procesebs,
umTavresad organul naerTTa gardaqmnebs warmoadgens.
Tanamedrove organuli qimia (bioorganuli qimia, bioqimia)
Seiswavlis organizmebis uj­redebSi mimdinare sasicocxlo
procesebs molekulur doneze da cdilobs axsnas sasicoc­
xlo procesebis urTule­si meqanizmebi da kanonzomiere­bani.
terminma `organuli qimia~ dReisaTvis ufro farTo
mniSvneloba SeiZina, vidre Tavdapirvelad iyo. amJamad
organuli qimia moicavs ara mxolod cocxal organizmebSi
Semaval nivTierebebs, aramed sinTezis gziT miRebul
nivTierebebsac, romelTac araviTari kavSiri ara aqvT cocxal
bunebasTan.
1. daasaxeleT yofacxovrebaSi gamoyenebuli niv­Tie­
rebebidan romelia organuli da romeli _ ara­
organuli.
2. daasaxeleT magaliTebi, romlebic adasturebs or­
ganuli da araorganuli naerTebis erTianobas.
saSinao davaleba
1. romeli qimiuri reaqciebiT SeiZleba organuli da ara­
organuli nivTierebebis erTmaneTisgan gansxvaveba?
2. moiZieT informacia qarTveli qimikos-organikosebis
Sesaxeb da gaakeTeT prezentacia.
7
I Tavi
organul naerTTa qimiuri aRnagobis Teoria.
eleqtronuli Teoria
§1. organuli naerTebis aRnagobis Teoria
organuli qimiis Teoriul safuZvels Seadgens organul
naerTTa qimiuri aRnagobis Teoria, romelic Seiqmna XIX s-is
60-ian wlebSi.
organul naerTTa qimiuri aRnagobis Teoria aris moZ­
Rvreba organul naerTTa molekulebSi atomTa SesaZlo
ganlagebisa da urTierTgavlenis Sesaxeb.
fridrih kekule
(1829-1896)
am Teoriis ZiriTadi arsi SeiZleba Camoyalibdes Semdegi
debulebebis saxiT:
1. molekulebSi atomebi ganlagebulia ara uwes­ri­god,
aramed erTmaneTTan SeerTebulia garkveuli Tan­
mimdevrobiT, maTi valentobis Sesabamisad. atomTa
SeerTebis rigs qimiuri aRnagoba ewodeba. organul
naerT­Ta molekulebSi naxSirbadis valentoba yovelTvis
4-is tolia.
arCibald kuperi
(1831-1891)
2. nivTierebaTa Tvisebebi damokidebulia ara mxolod
imaze, Tu romeli elementis atomebi da ra raodneobiT
Sedis maTi molekulebis SemadgenlobaSi, aramed mo­
lekulaSi atomTa SeerTebis Tanmimdevrobazec, e.i. mo­
lekulis qimiur aRnagobaze.
3. molekulis warmomqmneli atomebi an atomTa jgufebi
axdenen erTmaneTze gavlenas, razec damokidebulia
molekulebis reaqciisunarianoba. erTmaneTTan uSua­
lod dakavSirebul atomTa urTierTgavlena ufro
Zlieria.
aleqsandre
butlerovi
(1828-1886)
qimiuri aRnagobis Teoriis SeqmnaSi mniSvnelovani wvlili
Seitana germanelma qimikosma f. kekulem, Sotlandielma qimikosma
a. kuperma, rusma qimikosma a. butlerovma.
f. kekulem da a. kuperma daadgines naxSirbadis oTxvalentia­
noba organul naerTebSi, aseve gamoTqves mosazreba naxSirbadatomTa erTmaneTTan jaWvurad SeerTebis unarze. a. butlerov­ma eqsperimentis safuZvelze axsna izomeriis movlenis arsi da
miuTiTa molekulis agebuleba-Tvisebebis urTi­erTkavSirze.
8
qimiuri aRnagobis Teoriam mniSvnelovani roli Seasrula
organuli qimiis ganviTarebaSi. man axsna ara marto im
droisaTvis cnobil organul naerTTa molekulebis aRnagoba
da Tvisebebi, aramed SesaZlebeli gaxada mravali axali
nivTierebis winaswarmetyveleba da maTi sinTezis gzebis
Zieba.
organuli qimiis Semdgomi ganviTarebis procesSi qimiuri
aRnagobis Teoria Seivso stereoqimiuri da eleqtronuli
TeoriiT. stereoqimiuri Teoria Seiswavlis organul
naerTTa molekulebSi atomTa sivrciT ganlagebas, e.i.
molekulaTa sivrciT aRnagobas. eleqtronuli Teoria ki
arkvevs molekulaSi atomTa Soris qimiuri bmebis xasiaTs,
xsnis atomTa urTierTgavlenis arss da ama Tu im qimiuri
Tvisebis gamovlenis mizezs.
samive Teoriis erTianoba Seadgens organul naerTTa
aRnagobis Tanamedrove Teoriis arss.
saSinao davaleba
1. Tqveni TvalsazrisiT, ra mniSvneloba hqonda d.i. men­
de­leevis periodulobis kanonis aRmoCenas da organul
naerTTa qimiuri aRnagobis Teoriis Camoyalibebas
sabunebismetyvelo mecnierebebis ganviTarebis saqmeSi.
gaakeTeT prezentacia.
9
§2. eleqtronuli Rrublebis
hibridizacia organul naerTebSi
organul naerTTa molekulebi warmoadgens garkveuli
TanmimdevrobiT erTmaneTTan kovalenturi bmebiT dakav­
Sirebul atomTa erTobliobas, romelSic ZiriTadia
naxSirbadis atomebi.
gavixsenoT naxSirbadis atomis gare energetikuli donis
orbitalebze savalento eleqtronebis ganawileba ZiriTad
da aRgznebul mdgomareobaSi:
C
2s
↑
↑↓
2p
↑
→
C
2s
* ↑
↑
2p
↑
↑
savalento
Sreze oTxi gauwyvilebeli eleqtronis ar­
.
seboba (· С. ·) mis oTxvalentianobas ganapirobebs. Sesabamisi
eleqtronuli konfiguracia ase gamoisaxeba:
2s12px1 2py1 2pz1 ,
saidanac Cans, rom naxSirbadis atomSi kovalenturi bme­
bis warmoqmnaSi monawile eleqtronebi sxvadasxva mdgo­
mareobaSia: erTi eleqtroni s-orbitalze, sami ki p-or­
bitalzea. Sedegad unda warmoiqmnas aratolfasi bmebi,
romlebic erTmaneTisgan gansxvavdebian eleqtronuli
Rrublebis gadafarvis xarisxiT. aqedan gamomdinare, unda
gansxvavdebodnen bmis TvisebebiTac, rac eqsperimentulad
ar dadasturda.
am movlenis asaxsnelad amerikelma lainus polingma
mecnierebaSi Semoitana warmodgena eleqtronuli Rruble­bis (orbitalebis) hibridizaciis Sesaxeb. l. polingis
mixedviT bmis warmoqmnaSi monawileobs sawyisi orbitale­
bis SereviT miRebuli hibriduli orbitalebi. warmoqmnili
hibriduli orbitalebis ricxvi hibridizaciaSi monawile
sawyisi orbitalebis ricxvis tolia. hibridizaciaSi
monawileobs energiebiT erTmaneTisagan mcired gan­sxva­
vebuli (erTi ener­getikuli donis sxvadasxva qvedonis)
orbitalebi. Se­degad maTi energiebis gasaSualeba xdeba,
rac eleqtronuli Rrublis formis SecvlaSi gamoixateba.
hibriduli or­bitali asimetrulia, aqvs erT mxares
gawelili rvianis forma. bunebrivia, aseTi orbitalebiT
bmis damyarebisas arahibridul orbitalebTan SedarebiT
gadafarvis xarisxi metia. Sedegad hibriduli orbitale­biT ufro mtkice bmebi myardeba.
amrigad: hibridizacia aris gansxvavebuli formisa da
energiis orbitalebis erTmaneTTan Sereva
erTnairi formisa da energiis orbitalebis
warmoqmniT.
10
 gaixseneT, ra iciT
s-da p-orbitalebis
formisa da energiis
Sesaxeb
s-orbitali
p-orbitali
hibriduli
orbitali
erTi s- da sami p-orbitalis hibridizaciiT warmoqmnili
oTxi hibriduli Rrubeli sivrceSi maqsimaluri urTi­
erTganzidvis gamo, mimarTulia tetraedris wveroebisaken.
kuTxe maT Soris 109°28´-ia. hibridizaciis am saxes
sp3-hibridizacia ewodeba.
+
s
+
px
+
py
→
pz
109°28´
oTxi sp3-hibriduli
eleqtronuli Rrubeli
tetraedris wveroebisaken mimarTuli oTxi sp3-hibriduli
orbitaliT naxSirbadi kovalentur σ-bmebs amyarebs nax­
Sirbadis, an sxva elementis (magaliTad, wyalbadis, Jangbadis
da sxv.) atomebTan.
hibridizaciaSi yovelTvis monawileobs s-orbitali, p-or­
bitalebidan ki SeiZleba monawileobdes mxolod nawili. Tu
hibridizaciaSi monawileobs erTi s- da ori p-orbitali,
warmoiqmneba sami hibriduli Rrubeli, romlebic erT­
maneTisgan maqsimaluri dacilebiT, 120°-iani kuTxiT gan­
lagdebian erT sibrtyeSi. hibridizaciis am saxes sp2-hi­
bridizacia ewodeba.
+
+
→
120°
s
px
py
sami sp2-hibriduli
eleqtronuli Rrubeli
warmoqmnili sami sp2-hibriduli orbitaliT
naxSirbadi sam σ-bmas amyarebs sxva atomebTan
sibrtyeSi. mas rCeba erTi p-orbitali, romelic
inarCunebs moculobiT rvianis formas, lagdeba
sibrtyis marTobulad da mezobeli naxSirbadis an
Jangbadis atomis aseTive p-orbitalTan gverduli
gadafarviT warmoqmnis π-bmas.
Tu hibridizaciaSi monawileobs erTi s- da
erTi p-or­bitali, hibridizaciis am saxes ewodeba
sp-hibridizacia. warmoqmnili ori hibriduli
orbitali maqsimaluri urTi­erTganzidvis gamo
pz
erTi arahibriduli
eleqtronuli Rrubeli
C
C
π-bmis warmoqmna
11
lagdeba urTierTsapirispiro mimar­TulebiT, erTmaneTis
mimarT 180°-iT da or σ-bmas axor­cielebs sxva atomebTan.
+
s
→
px
180°
pz
py
ori arahibriduli
eleqtronuli Rrubeli
hibridizaciis gareSe darCenili ori p-orbitali urTierT­
marTobul sibrtyeSi warmoqmnis or π-bmas.
hibridizacia
geometriuli forma
savalento kuTxe
sp3
tetraedruli
109°28´
sp2
brtyeli samkuTxa
120°
sp
xazovani
180°
amrigad: atomTa eleqtornuli orbitalebis hibri­di­
zaciiT SesaZlebelia aixsnas nivTierebebis
qimiuri aR­nagoba, Ngeometriuli formebi, razec
Ziri­Tadad damokidebulia maTi Tvisebebi.
1. gaixseneT kovalenturi bmis saxeebi. kovalenturi bmis
warmoqmnaSi romeli orbitalebi monawileobs? moiyvaneT
magaliTebi.
saSinao davaleba
1. riTi iyo ganpirobebuli atomuri orbitalebis hibri­
dizaciis Teoriis Semotana qimiaSi da raSi mdgomareobs am
Teoriis ZiriTadi arsi?
2. hibridizaciis romel saxes Seesabameba naxSir­badatomTan
dakavSirebuli atomebis an atomTa jgufebis xazovani,
brtyeli da sivrciTi ganlageba?
12
C
C
π-bmebis
warmoqmna
§3. naxSirbadis atomTa Taviseburebani
eleqtronuli aRnagobis TeoriiT avxsnaT naxSirbadis
atomebis erTmaneTTan jaWvurad SeerTebis unari. nax­
Sirbadis atomis radiusi mcirea, oTxive savalento eleq­
tronis mowyveta birTvTan Zlieri mizidvis gamo Znelia,
aseve Znelia oTxi eleqtronis mierTeba gare energetiku­
li donis dasrulebisaTvis. amis gamo naxSirbadi TiTqmis
ar warmoqmnis ionur bmebs, magram advilad warmoqmnis
kovalentur bmebs. radgan eleqtronebis gacemisa da mier­
Tebis unari masSi TiTqmis Tanabrad vlindeba, kovalenturi
bmebi advilad myardeba naxSirbadis atomebs Sorisac.
kovalenturi bmebiT erTmaneTTan dakavSirebuli nax­
Sirbadis atomebi warmoqmnian sxvadasxva sigrZisa da aRnago­
bis xazovan, ganStoebul da ciklur jaWvebs:
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
naxSirbadis atomebs Soris bmis xasiaTic SeiZleba iyos
gansxvavebuli. naxSirbadatomebi erTmaneTs ukavSirdeba
ara marto martivi (erTmagi), aramed ujeri (ormagi, sammagi)
bmebiTac:
C
C
C
C
C
C
C
C
C
C
C
C
C
amrigad: organul naerTTa molekulebSi naxSirbadis
atomebs Soris mxolod kovalenturi bme­
bia: σ-bmebi warmoqmnilia hibriduli orbi­
talebiT, π-bmebi ki _ arahibriduli p-orbi­
talebiT. amave dros naxSirbadis atomebs
Soris bmebi arapolarulia, magram Tu nax­
SirbadTan bmas axorcielebs gansxvavebuli
eleqtrouaryofiTobis mqone atomi, bma po­
laruli xdeba. gaixseneT, polaruli bmiT
dakavSirebul atomebs gaaCnia nawilobrivi
muxtebi, rmlebic aRiniSneba berZnuli asoTi
delta (δ). atomi, romlis eleqtrouaryofiToba
13
ufro metia, Tavisken gadawevs bmis eleqtronul
simkvrives da Rebulobs nawilobriv uaryofiT
muxts (δ–). masTan dakavSirebul meore atoms ki
uCndeba eleqtornuli simkvrivis deficiti da
birTvis muxtis xarjze nawilobriv dadebiTad
(δ+) imuxteba.
● amis gaTvaliswinebiT, miuTiTeT, rogoria
mocemul bmaTa buneba da atomTa nawilobrivi
muxtebi: C – C
C–H
C – Cl
C – O.
zogierTi atomi an atomTa jgufi (Camnacvlebeli) iwvevs
naxSirbadovan jaWvSi eleqtronuli simkvrivis Secvlas _
gaZlierebas an Sesustebas (polarizacias). Tu Camnacvle­–
beli naxSirbadovan jaWvSi zrdis eleqtornul si­m­
kvrives, aseTi Camnacvlebeli eleqtrondonoruli bune­
bisaa (magaliTad, CH3), xolo Tu amcirebs _ igi eleqtron­
aqceptoruli bune­bisaa (magaliTad, Cl).
1. SeuZliaT Tu ara Si-is atomebsac, naxSirbadatomis
analogiurad, warmoqmnan erTnairi ato­mebisgan
Semdgari grZeli jaWvebi? SeadareT C – C da
Si – Si bmebi erTmaneTs da CamoayalibeT Tqveni
mosazreba.
saSinao davaleba
1. CamoayalibeT, ra
mravalferovnebas.
14
ganapirobebs
organul
naerTTa
§4. kovalenturi bmis gawyveta
organuli nivTierebebis urTierTqmedebas yovelTvis
Tan axlavs kovalenturi bmebis gawyveta da axali bmebis
warmoqmna.
SesaZlebelia kovalenturi bma ise gawydes, rom bmis
wamromqmneli eleqtronuli wyvili Tanabrad ganawildes
atomebs Soris. am dros warmoiqmneba nawilakebi, romelTac
aqvT gauwyvilebeli eleqtronebi:
A : B → A· + ·B
nawilaks, romelsac aqvs gauwyvilebeli eleqtroni,
radikali ewodeba, kovalenturi bmis simetrul gawyve­
tas ki _ radikaluri anu homolituri gawyveta.
SesaZlebelia kovalenturi bma ise gawydes, rom saerTo
eleqtronuli wyvili darCes erT romelime atomTan. am dros
warmoiqmneba ionebi:
+
–
A : B → A + : B
an –
+
A:B→A :+B
radgan kovalenturi bmis asimetrul gawyvetas Tan sdevs
ionebis warmoqmna, amitom bmis aseT gawyvetas ionuri anu
heterolituri gawyveta ewodeba.
amrigad:
arsebobs kovalenturi bmis gawyvetis orgvari
meqanizmi: radikaluri anu homolituri da
ionuri anu heterolituri. Tu romeli meqa­
nizmiT ganxorcieldeba bmis gawyveta reaq­ciis
mimdi­nareobisas, damokidebulia bmis bunebasa
da reaqciis Catarebis pirobebze.
1. CH3Cl molekulaSi C – Cl bmis homolituri gawvetisas
romeli nawilakebi warmoiqmneba?
saSinao davaleba
1. CH3OH molekulaSi C – O da O – H bmebis gawveta rogori
meqanizmiT SeiZleba ganxorcieldes?
15
§5. izomeria
naxSirbadis atomTa unari, SeuerT­dnen erTmaneTs da
sxva elementis atomebs gansxvavebuli TanmimdevrobiT,
ganapirobebs movlenas, romelmac izo­meriis saxelwodeba
miiRo. izomeriis movlena cnobili iyo qimiuri aRnagobis
Teoriis Seqmnamde. cnobili iyo niv­Tierebebi, romelTac er­
Tnairi Se­d­geniloba, magram gansxvavebuli Tvi­sebebi gaaC­
ndaT. am movlenas i. ber­celiusma izomeria uwoda (berZnuli sityva `izos~ tols niSnavs, `meros~ _ nawilaks). izomeriis
movlenas mec­nieruli axna misca aRnagobis Teoriam.
● organul qimiaSi, garda molekuluri formulebisa, gamoiyeneba
aRnagobis formulebi, romelsac struqturul formulebsac
uwodeben.
struqturuli formulebi gamo­saxaven molekulaSi atomTa
SeerTebis rigs. magaliTad, propanis molekuluri formulaa _
C3H8, struqturuli formula:
H H H
H
C
C
C
H
H H H
xSirad Caweris simartivisaTvis struqturul formulebSi
xazebiT aRniSnaven bmebs mxolod naxSirbadis atomebs Soris.
aseT formulebs Sekvecil struqturul formulebs uwodeben:
CH3 _ CH2 _ CH3.
qimiuri aRnagobis Teoriis ZiriTadi debulebebidan
gamomdinare, erTnairi molekuluri Sedgenilobis naerTebSi
SesaZlebelia atomTa SeerTebis Tan­mimdevroba iyos gan­
sxvavebuli. maga­liTad, propanisagan gansxvavebiT, butanSi
(C4H10) SesaZlebelia naxSir­badatomTa orgvari ganlageba:
CH3 _ CH2_ CH2 _ CH3
butani
(duRilis t = –0,5°C)
CH3 _ CH _ CH3
CH3
izobutani
(duRilis t = –11,7°C)
Tu aRnagobis Teoria marTebulia, unda arsebuliyo
TvisebebiT gansxvavebuli ori butani. im droisaTvis cnobili
iyo mxolod erTi butani. meore _ ganStoebuli aRnagobis
butani 1867 wels daasinTeza a. butlerovma da mas izobutani
uwoda. aRniSnuli sinTeziT a. butlerovma eqsperimentulad
daadastura aRnagobis Teoriis WeSmariteba da mecnieruli
axsna misca izomeriis movlenas.
16
amrigad: izomerebi nivTierebebia, romelTac gaaCniaT
erTi da igive Sedgeniloba, magram gansxvavebuli
aRnagoba da amis gamo gansxvavebuli Tvisebebi.
organuli qimiis Semdgomma ganviTarebam izomerebi
sruliad gansxvavebul Tvisebebis mqone nivTierebebs
Sorisac gamoavlina. magaliTad, eTilis spirtisa da dime­
TileTeris Sedgeniloba gamoisaxeba erTi da imave mole­
kuluri formuliT _ C2H6O, magram maTi fizikuri da
qimiuri Tvisebebi gansxvavebulia. eTilis spirti siTxea,
dimeTileTeri _ airi. eTilis spirti urTierTqmedebs
natriumTan, dimeTileTeri ar reagirebs natriumTan. es
naerTebi erTmaneTis izomerebia.
maTi struqturuli formulebi gamoisaxeba ase:
H
H
H
C
C
H
OH
H H
eTilis spirti
H
C
H
O
C
H
H
H
dimeTileTeri
arsebobs izomeriis ori saxe: qimiuri aRnagobis izomeria anu struqturuli izomeria da sivrciTi izomeria
(stereoizomeria).
struqturuli izomerebi Tavis mxriv iyofa:
1. naxSirbadovani jaWvis izomerebad;
2. jeradi bmebis an funqciuri jgufebis mdebareobis izo­
merebad;
3. klasTaSoris izomerebad.
stereoizomeriis erT-erTi saxeobaa geometriuli anu
cis-trans izomeria. (izomeriis am saxeebs, saTanado masalis
Sesabamisad, TandaTan SeiswavliT).
1. rogor xsnis organul naerTTa aRnagobis Teoria
izomeriis movlenas?
saSinao davaleba
1. dawereT naerTTa sruli struqturuli formulebi,
Tu maT Sekvecil struqturul formulebs Semdegi saxe
aqvs:
a) CH3 — CH(CH3)2;
b) CH3 — C(CH3)2 — CH3 .
2. dawereT eTilis spirtisa da dimeTileTeris Sekvecil
struqturuli formulebi.
17
§6. organul naerTTa klasifikacia
organul naerTTa klasifikacias axdenen naxSirbadovani
jaWvis aRnagobis, an molekulaSi funqciuri jgufis bunebis
mixedviT. naxSirbadovani jaWvis aRnagobis mixedviT arCeven
sam ZiriTad jgufs:
1. acikluri naerTebi _ Ria jaWviani naxSirwyalbadebi da
maTi nawarmebi:
CH3
CH3 — CH2 — CH3
CH3
C
CH2
CH3
CH3
CH
CH3
CH3
CH3
C
CH2
CH
CH2
C
OH
Cl
CH2
CH2
COOH
NH2
CH3
2. karbocikluri naerTebi, romlebSic ganasxvaveben:
a) aliciklur naerTebs _ ciklur (Sekruli jaWvis) nax­Sir­
wyalbadebs da maT nawarmebs:
CH2
CH2
H 2C
CH2
HC
CH2
H 2C
CH
H2C
CH2
HC
CH2
H2C
CH2
CH2
NH2
CH2
CH2
b) aromtul naerTebs da maT nawarmebs:
CH3
OH
CH3
3. heterocikluri naerTebi (cikluri naerTebia, romelTa
ciklebi naxSirbadis atomebis garda Seicavs sxva _ hetero
atomebsac) da maTi nawarmebi:
18
S
O
N
N
N
atoms an atomTa jgufs, romelic ganapirobebs
organul naerTTa damaxasiaTebel qimiur Tvisebebs,
e. i. maT funqciebs, funqciuri jgufi ewodeba.
funqciuri jgufebis bunebis mixedviT arCeven organul
naerTTa klasebs.
organul naerTTa klasebi
cxrili №1
funqciuri
jgufi
jgufis
saxelwodeba
naerTTa klasi
zogadi formula
– F, – Cl, – Br,
–I, (– HaI)
halogenebi
halogennawarmebi
R – Hal
– OH
hidroqsili
spirtebi
fenolebi
R – OH
Ar – OH
aldehidebi
C = O
karbonili
_C
=
O
OH
_C =
karboqsili
O
O–
O
=
H
O
=
ketonebi
R – C
R – C – R
karbonmJavebi
O
R – C =
OH
rTuli eTeri
(esteri)
O
R – C =
OR
– NO2
nitro-
nitronaerTebi
R – NO2
– NH2
amino-
aminebi
R – NH2
naerTs, romlis SedgenilobaSi mxolod erTi funqciuri
jgufia, monofunqciurs uwodeben, ori funqciuri jgufis
Semcvels _ bifunqciurs da a.S. sxvadasxva funqciuri jgufebis Semcveli naerTi heterofunqciuria.
19
II Tavi
naxSirwyalbadebi
naxSirwyalbadebi umartivesi organuli naerTebia, ro­
melTa molekulebi Sedgeba naxSirbadisa da wyalbadis ato­
mebisgan. maTi zogadi formulaa CxHy . naxSirwyalbadebi
SeiZleba davyoT or jgufad _ Ria jaWvian (aciklur) da
ciklur naxSirwyalbadebad.
naxSirwyalbadebi
Ria jaWviani
najeri
ujeri
(alkanebi)
(alkenebi,
alkinebi da
sxv.)
cikluri
cikloalkanebi
da sxv.
najeri naxSirwyalbadebi (alkanebi)
Ria jaWvian naxSirwyalbadebs, romelTa molekulebSi
naxSirbadis atomebs Soris mxolod martivi (erT­
magi) σ-bmebia, ewodeba najeri naxSirwyalbadebi, saer­
Ta­Soriso nomenklaturiT* ki – alkanebi. dabali reaq­
ciis unarianobis gamo maT xSirad parafinebsac (laT.
parum affinis _ mcire swrafva) uwodeben.
§7. alkanebis homologiuri rigi
umartivesi najeri naxSirwyalbadia meTani, romelic iwyebs
TvisebebiTa da aRnagobiT msgavs naerTTa rigs, romelsac
homologiuri rigi ewodeba. homologiuri rigis wevrebi _
homologebi erTmaneTisgan gansxvavdebian erTi an ramdenime
CH2 jgufiT, romelsac homologiuri sxvaoba ewodeba.
amrigad: aRnagobiTa da TvisebebiT msgavs nivTierebebs,
romlebic erTmaneTisgan gansxvavdebian erTi an
ramdenime CH2 jgufiT, homologebi ewodebaT.
alkanebis homologiuri rigis zogadi formulaa CnH2n+2,
sadac n naxSirbadatomTa ricxvia molekulaSi. am rigis
pirveli oTxi wevris saxelwodeba trivialuria (anu
IUPAC-is (International Union of Pure and Applied Chemistry – Teoriuli da gamoyenebiTi
qimiis saerTaSoriso kavSiri) mier SemoTavazebuli nomenklatura.
*
20
aromatuli
(arenebi)
SemTxveviTi), danarCeni homologebis saxelwodebebi ki
warmoqmnilia berZnuli da laTinuri ricxviTi saxelebidan
daboloeba `an~-is damatebiT. radganac alkanebis homo­
logiuri rigis pirveli wevri meTania, am rigs xSirad meTa­
nis homologiur rigsac uwodeben.
alkanebis homologiuri rigi:
formula
CH4
C 2H 6
C 3H 8
C4H10
C5H12
C6H14
C7H16
C8H18
C9H20
C10H22
cxrili №2
saxelwodeba
tlR°C
tdR°C
meTani
eTani
propani
butani
pentani
heqsani
heptani
oqtani
nonani
dekani da a. S.
–182,5
–183,3
–187,1
–138,3
–129,7
–94,3
–90,5
–56,8
–53,7
–29,7
–161,6
–88,6
–42,2
–0,5
+36,0
+68,7
+98,4
+125,7
+150,7
+174,0
1. SeadgineT molekuluri formula alkanisa, Tu misi
molekula Seicavs
a) 12 naxSirbadatoms; b) 32 wyalbadatoms.
saSinao davaleba
1. mocemuli formulebidan najers miekuTvneba:
C3H6, C2H4, C3H8, C4H6, C4H10 .
§8. izomeria da nomenklatura
alkanebis homologiur rigSi adgili aqvs struqturuli
izomeriis erT-erT saxes _ naxSirbadovani jaWvis izomerias.
meTans, eTans da propans izomerebi ar gaaCnia, butanidan
dawyebuli ki yvela alkans aqvs izomerebi. amasTan naxSir­
ba­dis atomTa ricxvis zrdasTan erTad maTi raodenoba
swrafad matulobs. gaixseneT ramdeni izomeris saxiT arse­
bobs butani? pentans gaaCnia 3 izomeri, heqsans _ 5, heptans _ 9, dekans _ 75 da a.S.
pentanis izomerebia:
a) CH3 – CH2 – CH2 – CH2 – CH3
b) CH3 – CH – CH2 – CH3 CH3
CH3
g) CH3 – C – CH3
CH3
21
imis mixedviT, Tu ramden atoms ukavSirdeba molekulaSi
mocemuli naxSirbadis atomi, igi SeiZleba iyos pirveladi,
meoreuli, mesameuli da meoTxeuli. magaliTad pentanis
b)-izomerSi priveli da meoTxe naxSirbadatomebi pirveladia,
mesame naxSirbadis atomi _ meoreuli, xolo meore _
mesameuli. g)-izomerSi ki meore naxSirbadatomi meoTxeulia.
danarCeni atomebi?
alkanis molekulaSi wyalbadis erTi atomis
H
. .
Camocilebis Sedegad rCeba atomTa jgufi CnH2n+1
:
:H
H
C
_ romelsac alkilis radikals uwodeben. mas aqvs
. .
meTani
erTi gauwyvilebeli eleqtroni da axasiaTebs
H
maRali reaqciisunarianoba. naxSirwyalbadis radi­
H
kalebis saxelwodeba warmosdgeba Sesabamisi al­ka­
. .
. radikali
nebis saxelwodebisagan daboloeba `an~-is `il~-iT
H : C
.
.
SecvliT.
meTili
cxrilSi moyvanilia zogierTi alkilis radikalis
aRnagoba da saxelwodeba:
cxrili №3
H
radikalis saxelwodeba struqturuli formulebi
meTilis
CH3 –
eTilis
CH3 – CH2 – an C2H5 –
propilis
CH3 – CH2 – CH2 –
izopropilis
CH3
CH3
CH –
saerTaSoriso nomenklaturiT ganStoebuli aRnagobis
alkanebis dasaxelebisas saWiroa Semdegi wesebis dacva:
1. irCeven yvelaze grZel, araganStoebul naxSirbadatomTa
jaWvs, romelic warmoadgens mTavar jaWvs. Tu alkanSi
aRmoCndeba ramdenime erTnairi sigrZis jaWvi, maSin
maTgan isaa mTavari, romelic Seicavs yvelaze met
Camnacvlebels.
2. mTavari jaWvis SerCevis Semdeg axdnen jaWvSi Semavali
naxSirbadatomebis danomvras im bolodan, romelTanac
ufro axloa Canacvlebuli jgufi. Tu es wesi ar gvaZlevs
calsaxa pasuxs, maSin danomvras awarmoeben ise, rom
CamnacvlebelTa
lokantebis
(im
naxSirbadatomTa
nomrebi, romlebTanac Canacvlebulia radikalebi) jami
iyos minimaluri.
3. Tu alkanis molekulaSi ramdenime sxvadasxva Camnacvle­
belia, maSin maT asaxeleben anbanuri TanmimdevrobiT
da uTiTeben TiToeuli maTganis lokants. erTnairi
Camnacvleblis arsebobis SemTxvevaSi Sesabamisi saxel­
22
wodebebis win maTi ricxvis mixedviT iwereba prefiqsi
di (ori), tri (sami), tetra (oTxi) da a.S. Tu ori erTnairi
radikali Canacvlebulia erTsa da imave naxSirbadis
atomTan, maSin saxelwodebaSi lokanti orjer meordeba.
4. bolos, mTavar jaWvSi arsebuli naxSirbadatomebis
ricxvis mixedviT asaxeleben naxSirwyalbads, romelic
safuZvlad udevs alkanis saxelwodebas. araganStoebul
naxSirbadatomTa jaWvis mqone naxSir­wyalbadis sa­
xelwodebas win emateba n (normaluri).
aRniSnuli wesebidan gamomdinare, zemoT moyvanili izo­
merebis saxelwodebebi iqneba a) n-pentani; b) 2-meTilbutani;
g) 2,2-dimeTilpropani.
saerTaSoriso nomenklaturis wesebis gaTvaliswinebiT
davasaxeloT alkani:
CH3
3
4
5
6
CH3 – C – CH – CH2 – CH3
2
CH2 CH3
1
CH3
3,3,4-trimeTilheqsani.
1. SeadgineT 3-eTil-3,4,5-trimeTilheptanis struq­
turuli formula da uCveneT pirveladi, meoreuli, mesa­meuli da meoTxeuli naxSirbadatomebi.
saSinao davaleba
1. daasaxeleT saerTaSoriso nomenklaturis mixedviT
CH3 CH3
CH3 – C – C – CH3
CH3 CH3
2. SeadgineT Sekvecili truqturuli formula naxSir­
wyalbadisa, romlis saxelwodebaa – 2,4,5,5-tetra­meTil­
oqtani.
3. dawereT alkanis formula, romlis molekulaSi 6 pir­
veladi naxSirbadatomia da ar aris masSi meoreuli da
mesameuli naxSirbadatomi.
23
§9. eleqtornuli da sivrciTi aRnagoba
Tqven ukve iciT, rogor gamoisaxeba naerTTa eleqtronuli
formulebi. magaliTad:
H
. .
H : C
. . : H H
H
. . H
. . H
. .
H : C
. . : C
. . : H
. . : C
H H H
alkanebSi naxSirbadatomebi σ-bmebs warmoqmnis sp3-hib­
riduli orbitalebiT, romlebic mimarTulia tetraedris
wveroebisaken. hibridul orbitalTa RerZebs Soris kuTxe
aris 109°28´. amgvarad orientirebuli orbitalebi mniS­
vnelovnad gadaifareba wyalbadis atomTa s-orbitalebiT,
rac iwvevs energiis didi raodenobiT gamoyofas da mtkice,
erTnairi Tvisebebis mqone oTxi qimiuri bmis warmoqmnas.
amrigad: meTanis molekulas tetraedruli aRnagoba aqvs.
es ganpirobebulia naxSirbadis hibriduli orbi­
ta­lebis tet­raedis wveroebisaken mimarTuli
orien­taciiT.
↑
↓
↑↓
→
↓
↑
↓
↓
↑↓
↑
↑↓
↑↓
↑
alkanis homologiuri rigis TiToeuli wevris molekulaSi
naxSirbadatomTa eleqtronuli konfiguracia meTanis nax­
Sirbadatomis eleqtronuli konfiguraciis msgavsia.
amitom eTanis molekula SeiZleba warmovidginoT, rogorc
erTi saerTo wveros mqone ori tetraedri. mesame tetraedis
dakavSireba moxdeba kuTxiT, romelic 109°28´-is toli
iqneba. amrigad, propanis, butanis da sxva naxSirwyalbadebis
molekulaSi naxSirbadatomebi erTmaneTs zigzagiseburad
ukavSirdeba.
109°28´
0,154 nm
naxSirbadatomebs SeuZlia Tavisuflad brunva martivi
σ-bmebis garSemo, amitom naxSirbadatomTa zigzagiseburma
24
meTanis molekulis
masStaburi modeli
meTanis molekulis
burTul-Rerovani
modeli
jaWvma SeiZleba sxvadasxva sivrciTi forma miiRos. maga­li­
Tad, pentanis molekulam SeiZleba Semdegi formebi miiRos.
5
1
2
3
5
4
a
1
3
2
4
1
5
4
2
3
b
g
energetikulad ufro xelsayrelia forma a, romelSic
wyalbadatomTa urTierTqmedeba minimaluria.
yvela es forma advilad gadadis erTmaneTSi, magram atom­
Ta bmebis Tanmimdevroba molekulaSi ucvleli rCeba.
1. gaixseneT, ramdeni saxis hibridizacias icnobT.
hibridizaciis romeli saxe vlindeba alkanebSi?
§10. miReba
alkanebis miRebis ZiriTadi wyaroa navTobi da bunebrivi
airi. navTobis fraqciuli gamoxdiT Rebuloben sxvadasxva
alkanis narevs. meTani warmoiqmneba mcenareul organizmeb­
Si Semavali celulozidan specifikuri mikroorganizmebis
gavleniT (e. w. `meTanuri duRili~). amis gamo igi gvxvdeba
daWaobebul adgilebsa da qvanaxSiris maRaroebSi (uwodeben
Waobis airs, maRaros airs).
bunebrivi wyaroebis garda alkanebis misaRebad iyeneben
sinTezur meTodebs. najeri naxSirwyalbadebis miReba
SeiZleba:
1. halogenalkanebis urTierTmqedebiT natriumTan (viur­
cis reaqcia). am reaqciiT SesaZlebelia naxSirbadovani jaWvis `dagrZeleba~.
CH3 – Br
CH3 – Br
R – Br
R – Br
+ 2Na → CH3 – CH3 + 2NaBr
+ 2Na → R – R + 2NaBr
2. karbonmJavaTa natriumis marilisa da natriumis hi­
droqsidis narevis SelRobiT. am reaqciiT SesaZlebelia
naxSirbadovani jaWvis `damokleba~. am xerxs iyeneben,
ZiriTadad, laboratoriaSi meTanis misaRebad:
CH3 – COONa + NaOH → CH4 + Na2CO3
R – COONa + NaOH → R – H + Na2CO3
25
3. meTanis miReba SeiZleba Aa) aluminis karbidis hidroliziT:
Al4C3 + 12H2O → 4Al(OH)3 + 3CH4.
b) naxSirbadis wyalbadTan urTierTqmedebiT:
→ CH + Q
C + 2H →
2
4
● ra pirobebSi unda Catardes mocemuli reaqcia, rom
wonasworoba gadaixaros meTanis wamroqmnis mxares?
 gaixseneT
le-Satelies
principi
1. ganaxorcieleT gardaqmnebi:
C2H5Cl → C4H10
C2H5COOH → ? → C2H6
§11. alkanebis Tvisebebi
fizikuri Tvisebebi. alkanebis homologiuri rigis pir­
veli oTxi wevri airia, Semdegi TerTmeti _ siTxe, xolo
heqsadekanidan (C16H34) dawyebuli _ yvela alkani myaria. airad
da myar alkanebs suni ar aqvT, xolo Txevadi alkanebis­Tvis
damaxasiaTebelia benzinis suni. sufTa saxiT isini uferulni
da wyalSi uxsnadebi arian, magram kargad ixsnebian organul
gamxsnelebSi.
aRsaniSnavia, rom alkanebis fardobiTi molekuluri masis
zrdasTan erTad kanonzomierad matulobs maTi duRilisa
da lRobis temperaturebi (cxr. №2). amasTan, araganStoe­
buli (normaluri) aRnagobis naxSirwyalbadebis duRilis
temperaturebi ufro maRalia, vidre maTi izomeruli gan­
Stoebuli naxSirwyalbadebisa.
● nebismieri naerTis duRilis temperatura ganisazRvreba
molekulebs Soris arsebuli mizidvis ZalebiT. arapolarul
naerTebSi (maT Soris naxSirwyalbadebSic) moqmedebs Zlier
susti molekulaTaSorisi mizidvis Zalebi, romlebic kidev
ufro sustdeba ganStoebis zrdasTan erTad, radgan moleku­
lebis daaxloeba da am Zalebis gamovlena Zneldeba. aqedan
gamomdinare, naerTis duRilis temperatura ecema.
qimiuri Tvisebebi. alkanebi (parafinebi) dabali reaq­
ciis unarianobiT xasiaTdebian. isini Cveulebriv pirobebSi
ar reagireben mJavebTan, tuteebTan da mJangavebTan. maTSi
atomebs Soris arapolaruli (C – C), an mciredpolaruli
(C – H) kovalenturi bmebia. maTi qimiuri gardaqmnebi mimdi­
nareobs am bmebis gawyvetis xarjze (krekingi), an wyalbadis
atomis sxva atomiT an atomTa jgufiT Secvlis xarjze
(Canacvlebis reaqciebi). radgan alkanebis moleku­lebSi
yvela valentoba gajerebulia, isini mierTebis reaq­ciebSi ar
Sedian.
26
1. wva. yvela alkani iwvis naxSirbad (IV) oqsidisa da wylis
warmoqmniT, amasTan meTani iwvis ufero aliT. meTanis
homologebSi naxSirbadis masuri wilis zrdasTan erTad alis
sikaSkaSe izrdeba. maRali wevrebi iwvian Wvartliani aliT.
(ratom?)
CH4 + 2O2 → 2CO2 + 2H2O
CnH2n+2 +
3n+1
O2 → nCO2 + (n+1)H2O
2
● meTanisa da Jangbadis (haeris) narevis anTebas
SeiZleba Zlieri afeTqeba moyves, Tu narevSi maTi
moculobiTi Sefardebaa 1:2 (10) (ratom?) amitom Zlier saSiSia
meTanis da haeris narevi qvanaxSiris maRaroebsa da binebSi.
2. Canacvleba.
a) halogenireba. alkanebisaTvis gansakuTrebiT dama­
xasiaTebelia Canacvlebis, kerZod ki halogenirebis, reaqciebi. isini aqtiurad reagireben fTorTan. oTaxis tem­
peraturaze sibneleSic ki reaqcia afeTqebiT mimdinareobs.
qlori­rebis reaqcia energiulad warimarTeba sinaTleze, an
maRal (250-400°C) temperaturaze sibneleSi. reaqcia brom­
Tan ufro Znelad xorcieldeba, xolo iodTan alkanebi ar
reagirebs.
ganvixiloT meTanis qlorirebis reaqcia:
H
H
H – C – H + Cl – Cl → H – C – Cl + HCl
H
H
H
qlormeTani
H
H – C – Cl + Cl – Cl → H – C – Cl + HCl
H
H
Cl
diqlormeTani
Cl
H – C – Cl + Cl – Cl → H – C – Cl + HCl
Cl
Cl
Cl
triqlormeTani (qloroformi)
Cl
H – C – Cl + Cl – Cl → Cl – C – Cl + HCl
Cl
Cl
tetraqlormeTani
(oTxqloriani naxSirbadi)
27
reaqcia mimdinareobs radikaluri meqanizmiT. sinaTleze
an gaxurebisas qloris molekula iSleba atomebad:
. .
. .
. . . .
:
:
: Cl
:
:
→
+
Cl
·
·
Cl
Cl
..
..
. . . .
warmoqmnili qloris atomi _ radikali, romelsac
gauwyvilebeli eleqtroni aqvs da Zlier reaqciisunariania,
moxleCs meTanis molekulas wyalbadis atoms, ris Sedegadac
warmoiqmneba qlorwyalbadi da meTilis radikali.
H
H
. .
. .
. .
. .
:
:
:
:
:
H : C
H
·
Cl
H
Cl
+
→
+
H
C
·
..
..
. .
. .
H
H
miRebuli meTilis radikali drois Zalian mcire
SualedSi arsebobs Tavisufali saxiT. igi reagirebs qloris
molekulasTan, warmoqmnis qlormeTans da qloris axal
radikals:
H
H
. .
. . . .
. .
. .
:
:
:
:
:
:
·
Cl
+
→
+
Cl
Cl
H
C
Cl
H : C
·
..
.. ..
. .
. .
H
H
qloris radikali, Tavis mxriv, urTierTqmedebs qlor­
meTanTan. miiReba qlorwyalbadi da axali radikali,
romelic agrZelebs process. amrigad, meTanis molekulaSi
TandaTanobiT xorcieldeba wyalbadatomTa Canacvleba
qloris atomebiT. reaqcia grZeldeba manamde, sanam ar Sew­
ydeba radikalebis warmoqmna. es ki SeiZleba moxdes rome­lime ori radikalis SeerTebiT (rekombinaciiT):
CH . + .CH → H C – CH Cl. + .CH → H C – Cl
3
3
3
3
3
3
reaqciebs, romlebic Tanmimdevrul gardaqmnaTa jaWvs
warmoadgens, jaWvuri reaqciebi ewodeba.
amrigad, qlorirebis reaqcia jaWvuri reaqciaa da mim­
dinareobs radikaluri meqanizmiT.
aRsaniSnavia, rom meTanis molekulaSi wyalbadatomis
qloris atomiT Canacvleba iwvevs danarCeni wyalbadatomebis
reaqciisunarianobis gazrdas da Semdgomi qlorirebis pro­
cesis gaadvilebas. es ganpirobebulia qloris atomis gavle­niT C –H bmebis simtkiceze. qloris atomis eleqtro­
uaryofiToba metia, vidre naxSirbadis atomisa, ris gamoc
C –C l bmis eleqtronuli simkvrive gadaiwevs qloris­ken.
bma polarizdeba da naxSirbadtomze Cndeba eleqtronuli
simkvrivis deficiti (eleqtornuli simkvrivis Semcireba),
romlis kompensacia xdeba C – H bmebis eleqtornuli sim­
kvrivis gadaweviT naxSirbadis atomisken:
H
H
C
H
28
Cl
es iwvevs am bmebis Sesustebas, ris gamoc qlormeTanis
molekulaSi momdevno wyalbad­atomis Canacvleba qloris
atomiT gacilebiT ufro advilad xorcieldeba, vidre
meTanSi. e.i. qloris atomis eleqtronaqceptoruli bunebis
gav­leniT meTilis jgufSi wyalbadatomebis reaqciis
unaria­noba izrdeba.
meTanis qlorirebis analogiurad mimdinareobs sxva al­
kanebis qlorirebac. amasTan, Canacvleba miT ufro advilad
xorcieldeba, rac ufro naklebad aris hidrogenizebuli
(nakleb wyalbadatomebTan aris bmuli) naxSirbadis atomi.
magaliTad:
CH3 – CH2 – CH3 + Cl2 → CH3 – CH – CH3 + HCl
Cl
2-qlorpropani
CH3 – CH – CH3 + Cl2 → CH3 – CCl2 – CH3 + HCl
Cl
2,2-diqlorpropani
da a. S.
3. krekingi. 500°C-ze ufro maRal temperaturaze alkanebis
gaxurebisas uhaero sivrceSi xdeba maTi daSla ufro
dabalmolekulur naxSirwyalbadebad (krekingi). alkanebis
krekingi mimdinareobs radikaluri meqanizmiT, Sedegad
miiReba najeri da ujeri naxSirwyalbadebis narevi.
magaliTad,
C2H6 + C2H4
CH3 – CH2 – CH2 – CH3 CH4 + C3H6
4. Termuli daSla. meTani 1400°C temperaturaze iSleba:
CH4 → C + 2H2
2CH4 → C2H2 + 3H2
5. dehidrireba. alkanebis dehidrireba (wyalbadatomebis
Camocileba) mimdinareobs maRal temperaturaze kata­
lizatoris Tanaobisas:
CH3 – CH3
300°C
Cr2O3
CH2=CH2+H2
6. izomerizacia. normaluri aRnagobis alkanebi gaxurebiT
katalizatorebis (AlCl3, AlBr3) Tanaobisas ganicdis izo­
merizacias:
CH3 – CH2 – CH2 – CH2 – CH3 → CH3 – CH – CH2 – CH3
CH3
29
1. meTanTan
bromi
reaqciaSi
Sedis
qloris
analogiurad. SeadgineT reaqciis tolobebi.
2. ratom ar Sedis alkani mierTebis reaqciaSi? pasuxi
daasabuTeT.
saSinao davaleba
1. rogor ganasxvavebT
saSualebiT?
meTans
wyalbadisagan
cdis
2. gansazRvreT alkanis formula, romlis 1 moculobis
wvisTvis sa­Wiroa rvajer meti moculobis Jangbadi.
3. rogor ganaxorcielebT gardaqmnebs:
C2H6 → ? → C4H10
imsjeleT.
§12. gamoyeneba
naxSirwyalbadebis
wvis
Sedegad
gaxsovdeT! meTanis arasruli wvisas
gamoyofili didi raodenobis siTbo
gamoiyofa mxuTavi airi CO, amitom
ganapirobebs maT gamoyenebas sawvavad.
gamaTbobeli, romelic bunebriv airze
am mizniT gamoiyeneba rogorc bunebrivi
muSaobs, srul wesrigSi unda iyos.
airi, romlis ZiriTadi komponentia
meTani, aseve propan-butanis narevi
(ga­Txevadebuli airi). Txevadi naxSir­
wyalbadebis narevi ixmareba sawvavad avtomanqanebsa da
TviTmfrinavebSi. parafinisagan (myari alkanebis narevi)
amzadeben sanTlebs. misi meSveobiT JRenTaven qaRalds,
romelic wyalgaumtari xdeba da gamo­iyeneba SesafuTad.
samedicino preparati – vazelinis zeTi alkanebis narevia,
romelTa molekulebSi naxSirbadatomTa ricxvi 15-s ar
aRemateba, xolo vazelini _ myari da Txevadi alkanebis
narevia, romelTa molekulebSi Tormetidan ocdaxuTamde
naxSirbadatomia.
alkanebis izomerizaciiT Rebuloben ganStoebuli aR­
nagobis naxSirwyalbadebs, romelTac iyeneben maRal­
xarisxovan benzinad da kauCukis warmoebaSi. parafinebis
kreking-JangviT Rebuloben karbomJavebs da maT bazaze
sapnebsa da sxva gamrecx saSualebebs.
didi praqtikurli gamoyeneba aqvs alkanebis halo­
gennawarmebs. qlormeTans iyeneben gamacivebel agentad
macivar-danadgarebSi. amave mizniT gamoiyeneba diqlor­
30
difTormeTani (freoni). diqlormeTani, triqlormeTani
da tetraqlormeTani ixmareba gamxsnelebad. triiodmeTani
(iodoformi), rogorc antiseptikuri saSualeba, gamoiyeneba
stomatologiur praqtikaSi da malamoebis dasamzadeblad.
qloreTani (tdR +12°C) SedarebiT susti gaci­vebisas siTxed
iqceva, romelic Cveulebriv temperaturaze qroldeba didi
raodneobiT siTbos STanTqmiT. misi es Tviseba gamoiyeneba
medicinaSi adgilobrivi anesTeziisaTvis.
samedicino
preparatebi
myari alkanebis narevi.
sanTeli
propani.
gaTxevadebuli airi
freoni.
gamacivebeli agenti
31
ginda, meti icode?!
cikloalkanebi (cikloparafinebi)
naxSirbadis atomebma sp3-hibriduli orbitalebiT
SeiZleba warmoqmnas ara marto Ria grZeli jaWvebi, ara­
med Sekruli ciklebic. ciklis Sekvris Sedegad naxSir­
badatomebTan dakavSirebuli wyalbadatomTa ricxvi mcir­
deba. aseTi naxSirwyalbadebis zogadi formulaa CnH2n.
maT cikloalkanebs uwodeben. cikloalkanebis umartivesi
warmomadgenelia ciklopropani. homologiuri rigis Sem­
degi wevrebia: ciklobutani, ciklopentani, cikloheqsani
da a. S.
CH2
CH2
CH2 CH
CH2
CH
2
2 C CHH
H
CH
C
2
CH
H
C
CH
2
2 2 HCH
CH2
H
C
CH
C
2
2
CH
2 2
2
H
C
CH
CH
2
2
H2C CH2 CH2
CH
C
CH
2 H22C H
2 2 CH
H
C
H
C
CH
2 CH
2
2
2
2
2 CH
2
H22C H2CHCH
H2C CHH2 CH2C
CH
H2CH
C HCH
2C2
C CHCH
H22CH
C HH22CH
2
C CH
2C 2H C CH2 CH
2C
CH
2 2 H22C HH
H
C
CH
2 2 CH
2
2
2
CH
2
2C CH
2
H2C 2 CH2 2
2
22
CH
2 CH
2
simartivisTvis asec gamosaxaven:
cikloalkanebis molekulebSi yvela naxSirbadatomi
qimiur bmebs sp3-hibriduli orbitalebiT warmoqmnis,
magram bmebs SoOris kuTxe ciklis zomazea damokidebuli.
mcire ciklebSi (ciklopropani, ciklobutani) es kuTxe
mniSvnelovnad gansxvavdeba tetraedruli kuTxisagan,
rac aRniSnul cikloalkanebSi daZabulobas iwvevs da maT
aramdgrads xdis.
ciklopropans medicinaSi iyeneben nar­kozisaTvis. ci­
klopentanis birTvi Sedis adamianis orga­nizmSi arsebuli
dabalmolekuluri bioregulatorebis SemadgenlobaSi.
cikloalkanTa umravlesoba gamoiyeneba organul sinTezSi,
gansakuTrebiT, praqtikuli mniSvneloba aqvs cikloheqsansa
da meTilcikloheqsans. maTi dehidrirebiT Rebuloben
benzolsa da toluols, romlebsac iyeneben saRebrebis,
samkurnalo preparatebisa da sxva mniSvnelovani naerTebis
misaRebad.
32