manana vardiaSvili
qimia
sarekomendacio wigni
maswavlebelTaTvis
XII klasi
gamomcemloba inteleqti
Tbilisi
§17. karbonmJavebi
teqstis davalebebi
CamoayalibeT najeri da ujeri karbonmJavas ganmarteba. saTanado magaliTebi
Cvens mier SemOoTavazebuli karbonmJavebis formulebidan SearCieT.
CH3 - COOH ZmarmJava
CH3 – (CH2)7 – CH= CH – (CH2)7 – COOH oleinmJava
CH2=CH – COOH akrilmJava
romeli maTganis Sesaxeb SegiZliaT TqvaT dabejiTebiT _ Sedis hidrirebis
reaqciaSi.
axseniT ratom.
najeri karbonmJava Seicavs najer radikals, ujeri ki – ujers. hidrirebis
reaqciaSi Seva akrilmJava da oleinmJava, radganac maT SedgenilobaSi Sedis ujeri
radikali.
gamoikvlieT ZmarmJavas qimiuri Tvisebebi.
ZmarmJava gaanawileT sam sinjaraSi. erTSi CauSviT Mg, meoreSi _ MgO,
mesameSi ki _ Na2CO3 an CaCO3 (carci).
daakvirdiT reaqciebis mimdinareobas.
SeadgineT reaqciaTa tolobebi. SeadareT ZmarmJavas qimiuri Tvisebebi
araorganuli mJavebis qimiur Tvisebebs, gamoitaneT daskvna.
2(CH3COO)H + Mg → Mg(CH3COO)2+H2
2(CH3COO)H + Mg O→ Mg(CH3COO)2+H2O
2(CH3COO)H + Na2CO3 → 2CH3COONa+H2O +CO2ZmarmJavas araorganuli mJavebis msgavsi Tvsebebi aqvs, magram is susti mJavaa,
araorganuli mJaveebidan mas SeuZlia mxolod susti naxSirmJavas gamoZeveba.
gamoikvlieT esterifikaciis reaqciis mimdinareobis pirobebi:
a) ZmarmJavian sinjaraSi CaasxiT eTilis spirti. amCnevT reaqciis niSnebs?
sinjara SeaTbeT:
amCnevT reaqciis niSnebs?
sinjaraSi mcireodeni gogirdmJavaa CaasxiT da sinjara kvlav SeaTbeT.
axla Tu amCnevT reaqciis niSnebs?
gamoitaneT daskvna esterifikaciis reaqciis mimdinareobis pirobebis Sesaxeb, Sei­
taneT aRniSvnebi reaqciis tolobaSi.
a) reaqciis niSnebi ar aris
b) reaqciis niSnebi ar aris
g) reaqcia mimdinareobs mxolod gacxelebisas da gogirdmJavas TanxlebiT
O
O
t
||
||
R – C – OH + R' – OH E R – C – OR' + H2O
H2SO4
teqstis Semdeg
1. SeadgineT erbomJavas
homologebisa da izomerebis or-ori formula, daasaxeleT isini.
CH3CH2CH2COOH erbomJava
106
erbomJavas homologebia:
CH3CH2CH2CH2COOH valerianmJava
CH3(CH2)4COOH kapronmJava
erbomJavas izomerebia:
O
CH3 – C
O – C2H5
eTilacetati
O
H–C
O – C 3H 7
propilformiati
2. saxelwodebis mixedviT SeadgineT nivTierebis struqturuli formula:
a) meTilacetati;
g) WianWvelmJava;
e) magniumis acetati;
z) eTilformiati;
O
a) CH3 – C
O
g) H – C
O – CH3
OH
d) Cl2CH – C
z) H – C
meTilacetati
WianWvelmJava
O
OH
O
b) mJaunmJava;
d) diqlorZmarmJava;
v) eTilacetati;
T) akrilmJava.
O – C 2H 5
b)
HO
C–C
O
OH
mJaunmJava
e) (CH3COO)2Mg – magniumis acetati
– diqlorZmarmJava
eTilformiati
O
v) CH3 – C
O
O – C2H5
– eTilacetati
T) CH2=CH2-COOH – akrilmJava
3. daasruleT reaqciaTa tolobebi
a) C17H35COOH+ NaOH →
b) C17H35COOH +Na2CO3 →
g) C17H33COOH +H2 →
a) C17H35COOH + NaOH → C17H35COONa + H2O
b) C17H35COOH + Na2CO3 → C17H35COONa + H2O + CO2g) C17H33COOH + H2 → C17H35COOH
4. sqemis Sesabamisad SeadgienT reaqciaTa tolobebi:
eTani → eTileni → bromeTani → eTanoli → Zmaraldehidi → ZmarmJava.
1) C2H6
–H2
C2H4 2) C2H4 +HBr→ CH3 – CH2Br 3) CH3 – CH2Br + NaOH→ CH3 CH2OH + NaBr
4) CH3CH2OH
[O]
CH3C
O
H
5) CH3C
O
H
[O]
CH3C
O
OH
5. Sedgenilobisa da agebulebis safuZvelze ivaraudeT akrilmJavas H2C=CH_
COOH qimiuri Tvisebebi.
107
H2C = CH – COOH am naerTs unda hqondes eTilenuri rigis naxSirwyalbadis
Tvisebebi da aseT reaqciebSi es naerTi Seva radikaliT. e. i. Seva mierTebis reaqciaSi,
magaliTad, hidrirebis reaqciaSi.
mas eqneba agreTve –COOH karboqsilis funqciuri jgufiT gamowveuli
karbonmJavas Tvisebebi. Seva magaliTad esterifikaciis reaqciaSi.
6. SeadgineT araorganuli nivTierebidan, magaliTad CO2-dan an CaC2-dan
ZmarmJavas miRebis sqema. Semdeg ki dawereT sqemis Sesabamis reaciaTa tolobebi.
CO2→ C → CH4 → C2 H2 → CH3 – C
1) CO2 + Mg → MgO+C
O
H
→ CH3 – C
O
OH
2) C + 2H2 → CH4
3) 2CH4→ C2H2+3H2
4) C2H2 + HOH→ CH3 – C
5) CH3 C
O
[O]
H
O
H
CH3 – C
O
OH
7. SeadgineT reaqciis sami toloba, romelTagan erTi – daasabuTebs WianWvelamJavas
msgavsebas ZmarmJavasTan, meore – daasabuTebs gansxvavebas WianWvelamJavasa da
ZmarmJavas Soris, mesame – daasabuTebs WianWvelamJavas da ZmarmJavas msgavsebas
araorganul mJavebTan.
1) H – C
2) H – C
5) H – C
O
[H]
OH
O
OH
O
OH
t
H–C
O
3) CH3 – C
H2O + CO2↑ 4) CH3 – C
H
O
OH
O
OH
[H]
CH3 – C
O
H
+ Mg → Mg(CH3COO)2
+Mg → Mg(HCOO)2
1) orive Sedis aRdgenis reaqciaSi.
2) WianWvelamJava gaxurebisas gogir­d­mJavas TanxmebiT moixleCs wylis mo­le­
kulas da iSleba naxSirorJangad da wylad.
3) araorganuli mJavebis msgavsad orive Sedis reaqciaSi metalebTan.
8. gamoTvaleT airis moculoba (n.p.) romelic SesaZloa gamoiyos 4.6 g metaluri
natriumis urTierTqmedebiT 0,1 mol meTanolTan.
0,1 moli
x
2HCOOH + 2Na → 2HCOONa + H2↑
2 moli 2 moli
1 moli
0, 1 x
4,6g
2 =1
ν (Na) = 23g/moli =0,2 moli Warbia 0,1 moli natriumi
x=0,05 moli H2
108
praqtikumi
sinjaraSi CaasxiT 1-2 ml ZmarmJava da daamateT TuTiis 1-2 granuli. amCnevT
Tu ara reaqciis niSnebs? sinjara odnav SeaTbeT.
a) ras amCnevT sinjaris SeTbobis Semdeg? riTi axsniT am movlenas?
b) romeli metalebi Seva reaqciaSi ZmarmJavasTan da romeli ara? axseniT
ratom.
a) sinjaraSi SeTbobis Semdeg reaqcia daiwyeba
b) ZmarmJavasTan reaqciaSi Seva mxolod aqtiuri metalebi.
§ 18. esterebi, cximebi
teqstis davalebebi
SeadgineT msxlis, vaSlisa da ananasis SemadgenlobaSi Semavali esterebis sax­
elwodeba.
msxlis esencia _ pentanbutanati
vaSlis esencia _ meTilbutanati
ananasis esencia _ eTilbutanati
teqstis Semdeg
1. SeadgineT iseTi esteris formula, romelSic naxSirbadatomTa minimaluri
ricxvia.
– daadgineT masSi TiToeuli elementis masuri wili.
– gansazRvreT, ra nivTierebisagan SeiZleba aseTi esteris miReba.
– SeadgineT Sesabamisi reaqciis toloba.
H–C
O
O – CH3
Mr (H – C
O
O – CH3
) = 60
w (H) = 4Ar (H) = 4 .
60
60
(
)
Ar
H
32 .
w (O) = 2
60 = 60
w (C) = 2Ar (C) = 24 .
60
60
am esteris miiReba SesaZlebelia WianWvelmJavasa da meTilis spirtis urTi­erT­qme­
debiT saTanado pirobebSi.
H–C
O
OH
+ CH3OH → H – C
O
O – CH3
+ H2O
2. daasruleT reaqciaTa tolobebi:
109
a) H3C – C
b) H3C – C
a) H3C – C
O
OH
O
OH
+ HOC2H5 →
+ HOCH2 – CH – CH3 →
O
OH
CH3
+ HOC2H5 → H3C – C
O
O – C2H5
O
+ HOCH2 –CH – CH3 → H3C – C
b) H3C – C
|
OH
CH3
+ H2O
O
O– CH2 – CH – CH3
|
CH3
+ H2O
3. ratom wvavs Tvalebs saponi?
sapnis hidroliziT miiReba tute, romelic wvavs Tvalebs.
4. rogor ganasxvavebT or, vardisfrad SemRvreul xsnars, Tu iciT, rom erT-erTSi
fenolia, meoreSi ki – saponi?
sapnis wyalxsnars tute reaqcia aqvs. amitom SesaZlebelia ganvasxvavoT
indikatoriT.
rodesac Tqveni mSoblebi skolaSi swavlobdnen...
80-90-ian wlebSi saqarTveloSi moqmed qimiis saxelmZRvaneloSi amoikiTxavT:
cximebi rTuli eTerebis klass ekuTvnian. amitom maTi yvelaze damaxasiaTebeli
reaqcia hidrolizia.
cximebis hidrolizis reaqcia, iseve rogorc sxva rTuli eTerebisa, Seqcevadia,
gamovsaxoT es gamartivebuli gantolebiT:
O
||
CH2 ― O ― C ―R
O
||
CH ― O ― C ― R
O
||
CH2 ― O ― C ―R
HO ― H
CH2 ― OH
O
+ HO ― H
D
CH ― OH + 3R ― C
OH
HO ― H
CH2 ― OH
ra pirobebi iqneba saWiro imisTvis, rom wonasworeobam glicerinisa da karnbonmJa­
vas warmoqmnis mxares gadainacvlos?
– upasuxeT cximebis hidrirebis reaqciis Sesaxeb dasmul SekiTxvas. axseniT Tqveni
pasuxi.
– kidev ra SegiZliaT TqveT cximebis qimiuri Tvisebebis Sesaxeb?
wonasworobam rom reaqciis produqtebis mxares gadainacvlos, mas atareben tute areSi,
risTvisac umateben metalis karbonats, magaliTad sodas Na2CO3 , an tutes. aseT pirobebSi
hidrolizi Seuqcevadad mimdinareobs da reaqciis Sedegad miiReba ara karbonmJava, aramed
misi marili.
110
ujeri mJavas naSTis Semcvel esters ujeri mJavas Tvisebebi aqvs – auferulebs bromian
wyals, Sedis SeerTebis reaciaSi. mniSvnelovania hidrirebis reaqcia, radgan am reaqciiT
Txevadi cximisagan myari esteri miiReba.
SeamowmeT Tqveni codna
1. kalciumis propionats bunebrivad Seicavs zogierTi saxeobis yveli,
zogierTs ki umateben specialurad, kvebiTi Rirebulebis gasaumjobeseblad.
a) saxelwodebis mixedviT SeadgineT am naerTis formula.
b) aRwereT, ra gziT SeiZleba misi miReba laboratoriaSi. SeadgineT reaqciis
toloba.
g) ivaraudeT da reaqciis tolobiT asaxeT misi Tvisebebi.
C3H7COOH _ propanmJava
(a) Ca(C3H7COO)2 _ kalciumis propionati
miReba:
(b) 2C3H7COOH + Ca → Ca(CH3COO)2 + H2
g) (C3H7COO)Mg + 2HCl → C3H7COOH + MgCl2
(C3H7COO)Mg + NaOH → Na(C3H7COO) + Mg(OH)2
2. Txis rZe erTfuZian karbonmJavas Seicavs, romelSic eqvsi naxSir­bad­
atomia.
– SeadgineT am naerTis struqturuli formula.
– ra hqvia am naerTs saerTaSoriso nomenklaturis mixedviT?
– romeli ukeT gaixsneba wyalSi – Txis rZe, Tu Zroxis rZe, romelic Seicavs
rZemJavas?
CH3CHCOOH
|
OH
– ra msgavsi da gansxvavebuli Tvisebebi aqvT am nivTierebebs?
– CamoayalibeT kriteriumebi, romlebic Sefasebisas gamoiyeneT.
O
CH3 – CH2 – CH2 – CH2 – CH2 – C
OH
_ heqsanmJava
_ ukeT gaixsneba rZemJava, imitom, rom masSi naxSirbadatomTa naklebi ricxvia da
Seicavs spirtul jgufs.
_ orive Seicavs karboqsilis jgufs, orives eqneba mJavebis Tvisebebi;
gansxvavebuli is aris, rom rZemJavaSi spirtuli jgufic aris da mas spirtis Tvisebebic
eqneba.
_ kriteriumi, Sedgeniloba da Tvisebebi.
3. suraTze Tqven xedavT qolesterinis struqturul formulas. naerTTa
romel klass miakuTnebdiT mas? ivaraudeT, unda ixsnebodes Tu ara wyalSi es
naerTi, daasabuTeT Tqveni varaudi. Cven ki dasaxmareblad gTavazobT spirtebis
wyalSi xsnadobis cxrils.
111
CH3
CH3
HO
H
HO
H
CH3
CH3
spirti
wyalSi xsnadoba
250C‑ze g/100 g
wyalSi
meTanoli
srulad ixsneba
eTanoli
srulad ixsneba
1 – propanoli
srulad ixsneba
1 – butanoli
9
cikloheqsani
5,6
1-heqsanoli
0,6
3. es naerTi Seicavs hidroqsilis jgufs, romelic ciklur naxSirwyalbadTan
aris dakavSirebuli. amis gamo is spirtis msgavsi naerTia, mxolod sakmarisad rTuli
Sedgenilobis radikaliT. radikalis sididisa da Sedgenilobidan gamomdinare
is wyalSi ar unda ixsnebodes, cxrilidan Cans, rom radikalis zrdasTan erTad
spirtebis xsnadoba mcirdeba.
4. sqemaze aRwerilia fenolidan samkurnalo preparatebis, aspirinisa da
dispirinis miReba:
a) romeli xerxia ufro ekonomiuri?
b) dispirini ukeT gaixsneba wyalSi Tu aspirini? (varaudis eqperimentiT
Semowmeba Zneli ar aris. orive preparati afTiaqSi iyideba).
g) erT-erTi maTgani ufro efeqturi tkivilgamayuCebeli saSualebaa, Ses­
aZlebelia, Tu ara is faqti maT wyalSi xsnadobas ukavSirdebodes? axseniT
amis mizezi.
a) cxadia ufro ekonomiuri meore xerxia, radgan CO2 iafi nedleulia da
erTsafexuriani procesic ufro ekonomiuria.
b) wyalSi ukeT gaixsneba dispirini, imitom, rom ionuri naerTia.
g) SesaZlebelia vivaraudoT, rom radgan dispironi wyalSi ukeT ixsneba, organizmSi
ukeT Seiwoveba xsnaris saxiT, amitom ufro efeqtiani tkivilgamayuCebelia.
112
§19 naxSirwylebi
teqstis davalebebi
glukozis molekuluri formulaa C6H12O6.
SeecadeT glukozis struqturuli formulis Sedgenas. gaiTvaliswineT, rom
naxSirbadis eqvsi atomidan erTi Sedis aldehidis jgufSi, darCenil xuT atomTan
ki TiTo spirtuli jgufia SeerTebuli.
CH2 – CH – CH – CH – CH – C
|
|
|
|
|
OH OH OH OH OH
O
H
glukoza Sedis reaqciaSi spilenZ(II)-is hidroqsidTan da glicerinis msgavsad kaS­
kaSa – lurji feris xsnars warmoqmnis.
glukoza warmoqmnis esterebs.
daasabuTeT am ori mosazrebis marTebuloba Teoriuli mtkicebulebis safuZvelze.
erTi maTgani mainc daasabuTeT eqsperimentulad.
glukoza mravalatomiani spirtia, amitom is reaqciaSi Sedis spilenZis
hidroqsidTan, es mravalatomiani spirtebis TvisebiTi reaqciaa. glukoza
warmoqmnis estersac, rogorc spirti. (eqsperimentis Casatareblad, ix. praqtikumi,
saxelmZRvanelo gv 120)
SeadgineT glukozis aRdgenis reaqciis toloba, Tu aRmdgenad gamoiyeneba wyal­
badi, reaqciis Sedegad ki miiReba eqvsatomiani spirti. reaqciis katalizatoria Ni.
O
+ [H] → CH2 – CH – CH – CH – CH – CH2OH
CH2 – CH – CH – CH – CH – C
|
|
|
|
|
H
|
|
|
|
|
OH OH OH OH OH
CH OH OH OH OH
teqstis Semdeg
1. SeiZleba Tu ara glukozis wrfivi forma CaiTvalos cikluri formis
izomerad. pasuxi daasabuTeT.
glukozis wrfivi da cikluri forma izomerebi ara aris, radgan izomerebi
damoukidebuli nivTierebebia, mxolod maTTvis damaxasiaTebeli fizikuri da
qimiuri TvisebebiT. glukozis wrfivi da cikluri formis arseboba pirobebzea
damokidebuli da maT erTi da igive Tvisebebi aqvs.
2. SeadareT glukozisa da glicerinis Tvisebebi, Sedarebis Sedegi gamosaxeT
diagramiT.
myari
nivTiereba,
aqvs rogorc
spirtis ise,
aldehidis
Tvisebebi
orive
mraval
atomiani
spirtia
siTxea.
aqvs
mraval­
atomiani
spirtis
Tvisebebi
113
3. sorbiti eqvsatomiani spirtia, misi miReba SesaZlebelia glukozisagan.
SeadgineT am reaqciis toloba. miuTiTeTM rogor SeiZleba sorbitSi spirtis
funqciu­ri jgufebis aRmoCena?
O
CH2 – CH – CH – CH – CH – C
+ H2 → CH2 – CH – CH – CH – CH – CH2
|
|
|
|
|
|
|
|
|
|
|
H
OH OH OH OH OH
OH OH OH OH OH OH
spirtuli jgufis aRmoCena SesaZlebelia spilenZis hidroqsidiT, mravalatomiani
spirtebis TvisebiTi reaqciiT.
4. 59 g glukozis sruli daJangvisas gamoiyo 146,3 kj siTbo. gamoTvaleT am reaqciis
siTburi efeqti.
146, 3kj.
59 g.
C 2 H 12 O 6 + 6O 2 " 6H 2 O + 6CO 2 + x
180g.
1 59
moli
180 g/mol
146, 3kj.
C59
6O 2 " 6H180
O 6CO
x
146
2 H 12 O
6 +, 3
x = 2 +$ 146, 32 +. 438, 9kj.
180180= x
59
146, 3
59
x = 180 $ 146, 3 . 438, 9kj.
180 = x
59
praqtikumi
1) eqsperimantis msvlelobisas miiReba vercxlis sarkis reaqcia, rac dakav­
Sirebulia glukozis molekulaSi aldehidebis jgufis arsebobasTan. aldehidis
jgufi arsebobs glukozis Ria formaSi, amitom vercxlis sarkis reaqcia
axasiaTebs glukozis Ria formas
CH3OH – (CHOH)4 – C
O
H
+ Ag2O
t
CH2OH – (CHOH)4 – C
O
H
+ 2Ag.
2) g) warmoqmnili spilenZ(II)-is hidroqsidis naleqi imitom gardaiqmneba lurji
fe­ris gamWvirvale xsnarad, rom mJRavndeba mravalatomiani spirtis Tvisebebi _
es aris TvisebiTi reaqcia mravalatomian spirtebze. am cvlilebas iwvevs spirtuli
jgufebi.
d) gacxelebisas iwyeba reaqcia glukozis alidehidis jgufTan. am
axladwarmoqmnili spilenZis hidroqsidiT iJangeba aldehidis jgufi, spilenZ(II)is hidroqsidi jer gardaiqmneba spilenZ(I)-is hidroqsidad, Semdeg ki spilenZ(I)-is
oqsidaT, romelic wiTeli ferisaa. wiTeli naleqi spilenZ(I)-is oqsidia.
O
O
+ Cu(OH)2 t
CH2OH – (CHOH)4 – C
+ Cu2O↓ + H2O
CH2OH – (CHOH)4 – C
H
OH
§20 disaqaridebi
1. ori uetiketo WurWlidan erT-erTSi myari sapnis fxvnilia, meoreSi ki – saxame­
beli. rogor ganasxvavebT maT erTmaneTisagan?
sapnis fxvnili wyalSi gaixsneba, saxamebeli ki ara. sapnis wyalxsnars tute reaqcia
aqvs. saxamebelis ki ara. saxamebelis xsnari gacxelebisas warmoqmnis bubkos, sapnis
xsnari ara.
2. rogor daamtkicebT, rom mwife vaSlSi aris glukoza, mkvaxe vaSlSi ki ar aris.
glukozisaTvis damaxasiaTebelia vercxlis sarkis reaqcia, amitom, am TvisebiT
reaqciiT SesaZlebelia mwife vaSlis wvenSi aRmovaCinoT glukoza. vaSlis wveni da
114
vercxlis oqsidis amiakiani xsnari gavacxeloT mduRare mzis abazanaze.
3. sityvebis nacvlad CawereT im nivTierebaTa formulebi, romelTa saSualebiTac
SesaZlebelia aRniSnuli gardaqmnebis ganxorcieleba.
ricxvebis nacvlad ki miuTiTeT saWiro reagentebi:
saxamebeli
glukoza
eTanoli
Zmris aldehidi
ZmarmJava
magniu­
mis acetati.
1. – hidrolizi gogirdmJavas monawileobiT.
2) spirtuli duRili; 3) kaliumis permanganati.
4) daJangva vercxlis oqsidis amiakiani xsnariT.
5) magniumi.
hidrolizi
spart.
KMnO
(C 6 H 10 O 5 ) n
nC 6 H 12 O 6 duRili C 2 H 5 OH
4
Ag 2 O
amiakiani
xsnari
CH 3 - C
O
O
OH
OH
CH 3 - C
O
O
"
H
H
4. ratomaa moxarSuli kartofili webovani? daasabuTeT Tqveni mosazreba.
moxarSuli kartofili imitomacaa webovani, rom kartofili Seicavs saxamebels da
misi xarSvisas miiReba deqstrinebi – saxameblis nawilobrivi hidrolizis produqti.
5. mxolod fizikuri Tvisebebis safuZvelze rogor ganvasxvavoT xorblis fqvili
saxameblisagan?
saxamebeli xeliT Sexebisas srialaa, xorblis fqvili ki ara. amave dros saxamebeli
ufro TeTria. saxameblis bubkoc gansxvavdeba xorblis fqvilis bubkosagan.
6.ra garegnuli niSnebi eqneba qvemoT aRweril reaqciebs:
a) kaliumis iodidis ufero xsnars daamates saxameblis bubko;
b) iodis spirtxsnars daamates saxameblis bubko;
g) natriumis iodidis ufero xsnars daamates, qloriani wyali, Semdeg ki saxameblis
bubko?
a) am SemTxvevaSi araviTari qimiuri efeqti ar iqneba, radgan saxamebelTan
reaqcias iZleva Tavisufali iodi.
b) am SemTxvevaSi iodi galurjdeba.
g) qlori gamoaZveebs iods, romelic saxamebelTan Sexebisas galurjdeba.
2NaI+Cl2 → 2NaCl+I2
7. ra masis saqaroza SeiZleba miviRoT1,5 t Saqris Warxlidan, Tu masSi saqarozas
masuri wili 20 % -ia?
1.5 t WarxalSi iqneba 1500 · 20% = 300 kg Saqari.
100
115
§21. aminebi
teqstis davaleba
uwodebdiT Tu ara pirvelad, meoreul da mesameul amins erTmaneTis izo­
merebs? daasabuTeT Tqveni varaudi Cven mier SemoTavazebuli magaliTebis ganx­
ilvis safuZvelze.
am magaliTebis mixedviT pirveladi, meoreuli da mesameuli amini erTmaneTis
izomerebia, radgan maT erTnairi molekuluri formula, anu erTnairi Sedgeniloba
da sxvadasxva agebuleba aqvs. (Tumca zogadad pirveladi amini magaliTad, CH3NH2
meTilamini trieTilaminis an dieTilaminis izomeri ar aris).
teqstis Semdeg
1. SeadgineT propileTilaminis izomerebis struqturuli formulebi.
C3H7
1. C2H5
NH
CH3 – CH2 – CH2
CH3 – CH2
NH
CH3
a) |
CH
–
C
– CH2 – NH2
3
|
CH3
b) CH3 – CH2 – CH2 – CH2 – CH2NH2
g) CH3 – CH2 – CH2 – CH2 – CH2 – NH2
|
CH3
d) CH3 – CH2 – CH – CH2 – NH2
|
CH3
e) CH3 – CH2 – CH2 – CH – NH2
|
CH3
CH3
v) |
CH3 – CH – NH
|
CH2 CH3
z)
C2H5
C2H5
N – CH3
T) C3H7 – N – CH3
|
CH3
2. fuZe Tvisebebis zrdis mixedviT ganalageT nivTierebebi:
CH3NH2 , NH3 , (CH3)2NH, C6H5NH2 .
C6H5NH2∠ NH3∠ CH3NH2∠ (CH3)2NH
benzolis birTvis gavleniT anilinis fuZe Tvisebebi CamorCeba amiakisas, xolo
alkilis radikalis gavleniT meTilaminSi da dimeTilaminSi fuZe Tvisebebi izrdeba
amiakTan SedarebiT.
3. SeadgineT meTanidan anilinis miRebis gardaqmnaTa sqema yvela Sualeduri
produqtis miTiTebiT, Semdeg ki dawereT reaqciaTa tolobebi.
CH4 → C2H2 → C6H6 → C6H5NO2 → C6H5NH2
a) 2CH4 → C2H2+3H2
116
b) 3C2H2 → C6H6
g) C6H6+HONO2
d)
[H2SO4]
6H
C6H5NO2 Zn + HCl
C6H5NO2+H2O
C6H5NH2+2H2O
4. ramdeni grami anilinis miReba SeiZleba 210 g nitrobenzolisagan, Tu am
reaqciis praqtikuli gamosavlianoba Teoriulis 75%-ia?
210
x
x = 210 $ 93 = 186 g.
105
C 6 H 5 NO 2 " C 6 H 5 NH 2 1 105
moli
105 g/mol
93
1 moli
93 g/mol
x = 186 $ 75 = 186 $ 3 = 139, 5 g
4
100
5. rodesac Tqveni mSoblebi skolaSi swavlobdnen
80-90-ian wlebSi saqarTveloSi moqmed qimiis saxelmZRvaneloSi aminebis Sesaxeb
weria:
azoti organul naerTebSi SeiZleba Sediodes ara mxolod azotmJavas naSTis
saxiT (gaixseneT nitrobenzoli C6H5NO2 da celoluzis rTuli eTeri _ trini­
trati [C6H7O2ONO2]3)11, aramed sxva formiTac. cnobilia mravali organuli naerTi,
romelSic azoti amiakis saxiT Sedis, magaliTad,
CH3 – N
H
H
meTilamini
CH3
C2H5
N–H
meTileTilamini
CH3
CH3
N–H
dimeTilamini
C6H5 – N
CH3
CH3
CH3
trimeTilamini
H
C6H5
H C6H5
fenilatmini (anilini)
N
N–H
difenilamini
yvela es naerTi aminebis klass ekuTvnis.
aminebi SeiZleba ganvixiloT rogorc amiakis nawarmebi, romelTa moleku­
laSi wyalbadis erTi an ramdenime atomi Canacvlebulia naxSirwyalbadebis radi­
kalebiT.
sityvierad CamoayalibeT, ra iciT ufro meti aminebis agebulebis, izomeriisa da
nomenklaturis Sesaxeb.
R
R
amini SesaZloa iyos pirveladi R – NH2 , meoreuli
NH da mesameuli R N , Tu
R
R
aminojgufi uSualodaa dakavSirebuli aromatul birTvTan miiReba aromatuli amini.
aminebSi arsebobs naxSirbadovani ConCxis izomeria da funqciuri jgufis mdebareobis
izomeria. magaliTad,
CH3 – CH2 – CH2 – CH2NH2
da
CH3 – CH2 – CH2 – NH2
CH3 – CH – CH3
|
NH2
da
CH3 – CH – CH2 NH2
|
CH3
117
§22. aminomJavebi
teqstis Semdeg
1. SeadgineT reaqciaTa tolobebi, romlebic asaxavs aminopropanmJavas urTierT­
qmedebas
a) gogirdmJavasTan;
b) meTilis spirtTan;
g) natriumis hidroqsidTan.
O
NH2 – CH2 – CH2 – C
– aminopropanmJava
OH
a) H2SO4+2(NH2 – CH3 – CH2 – C
b) NH2 – CH2 – CH2 – C
g) NH2 – CH2 – CH2 – C
O
OH
O
OH
O
OH
) → [HOOC – CH2 – CH2 – NH3]2 SO42–
+HOCH3 → N2H – CH2 – CH2 – C
+ NaOH → N2H – CH2 – CH2 – C
O
O – CH3
O
O – Na
2. SeadgineT ε-aminokapronmJavas polikondensaciis reaqciis toloba, Tu misi for­
mulaa:
H2N – (CH2)5 – C
O
OH
H2N – (CH2)5 – C
O
OH
O H
+ H2N – (CH2)5 – COOH → H2N – (CH2)5 – C – N – (CH2)5 – COOH + H2O
3. SeadgineT dipeptidis warmoqmnis reaqciis toloba aminoZmarJava da α-ami­no­pro­pi­
onmJavasgan.
NH2 – CH2 – C
H2N – CH – C
|
CH3
O
OH + NH2 – C
O
+ H2N – CH – C
|
OH
CH3
aminoZmarmJava 118
→ NH2 – CH2 – C – N – CH2 – C
|| |
O H
O
→ H2N – CH – C
OH
|
CH3
a – aminopropanmJava
O
O
OH
CH – C
N
|
| CH3
H
O
OH
+ H2O
4. SeadareT polimerizaciis da polikondensaciis reaqciebi, Sedarebis Sedegebi asax­
eT diagramiT.
polimerizacia
Tanauri
produqti
ar gamoiyofa
polikondensacia
Tanauri
mimdinareobs
sawyisi mo­
produqtebi
gamoiyofa.
no­merebis
Se­erTebiT.
§23. cilebi
teqstis Semdeg
1. ra mimarTeba arsebobs cnebebs Soris: `peptidi~, `polipeptidi~, `poliamidi~,
`cila~.
aminomJavebis erTmaneTTan urTierTqmedebis Sedegad miiReba maRalmolekuluri
naerTi polimeri, romelic amiduri fragmentebis did raodenobas Seicavs, amitom
ewodeba poliamidi. amiduri dajgufebaa – CO – NH –, a_aminomJavebisagan warmoqmnil
O H
|| |
poliamids polipeptidi ewodeba, xolo – C – N – dajgufebas polipeptidis mo­le­
kulaSi pep­tiduri dajgufeba ewodeba.
50-ze meti a–aminomJavasagan Sedgenili polipeptidi ukve cilaa.
2. SeadgineT reaqciis toloba, romelic Seesabameba cilis hidrolizs, Tu misi
zogadi formulaa:
– NH – CH – CO –
|
R
axseniT, ra mniSvneloba aqvs am process adamianis organizmisaTvis.
O
– NH – CH – CO – n·H O nH2N – CH – C
OH
|
|
R
R
cilis hidrolizis dros warmoiqmneba aminomJavebi. saWmlis monelebisas fer­
men­tebis gavleniT xdeba cilebis hidrolizi. kuWSi isini ixliCeba polipeptidebad,
romlebic Semdeg nawlavebSi aminomJavebamde hidrolizdeba. warmoqmnili amino­mJa­
vebi, nawlavebis xaoebiT sisxlSi Seiwoveba da organizmis yvela qsovilsa da ujreds
miewodeba.
2
3. moifiqreT da aRwereT meTodi, romliTac martivad ganasxvavebT:
– Salis Zafs bambis Zafisagan
– xelovnur abreSums bunebrivisagan
axseniT, ras efuZneba Tqvens mier gamoyenebuli meTodi.
Salis Zafi Seicavs cilovani warmoSobis boWkos. bamba ki celoluzaa, Salis
Zafis dawvisas iqneba specifikuri suni, rac ar SeimCneva bambis Zafis dawvisas.
bunebrivi abreSumic Seicavs cilovani warmoSobis boWkos, misi dawvis drosac iqneba
specifikuri suni, rac ar SeimCneva xelovnuri abreSumis dawvisas.
119
§ 24. polimerebi
Sidateqturi
gTavazobTeTilenis polimerizaciis sqemas.
nCH2=CH2 → (...– CH2– CH2 –...)n
am sqemis magaliTze gaixseneT cnebebi: po­li­meri, monomeri, monomeruli
erTeuli, poli­me­ri­zaciis xarisxi. ras aRniSnavs n po­limerizaciis re­aqciis
sqemaSi? ra gansxvavebaa monomersa da mo­no­merul erTeuls Soris?
polimeri aris maRalmolekuluri nivTiereba, romelic miiReba dabalmolekuluri
monomerebis SeerTebis Sedegad. monomeri dabalmolekuluri nivTierebaa, romlisaganac polimeri warmoiqmneba. monomeruli erTeuli atomTa dajgufebaa, romelic
makromolekulaSi meordeba. polimerizaciis xarisxi gviCvenebs makromolekulaSi
monomeruli erTeulebis ricxvs.
teqstis Semdeg.
SesaZlebelia Tu ara monomerul erTeulad miviCnioT polieTilenis
molekulebSi – CH2 – jgufi, pasuxi daasabuTeT.
_ CH2 _ jgufi monomeruli erTeuli ar aris, miuxedavad imisa, rom is jaWvSi mravaljer meordeba. monomeri aris aseTi Sedgenilobis CH2=CH2, monomerul erTeuls ki
aseTi Sedgeniloba aqvs:
_ CH2 _ CH2 _
2. ras aRniSnavs n vinilqloridis polimerizaciis reaqciaSi?
n CH2 = CH
– CH2 – CH –
n
Cl
Cl
n aRniSnavs polimerizaciis xarisxs, anu makromolekulaSi monomeruli erTeulebis raodenobas
3. polieTilenis saSualo molekuluri masaa 28000. gamoiangariSeT misi
polimerizaciis xarisxi.
Mr(CH2=CH2)=28
n=28000:28=1000.
4. mecnierebi miiCneven, rom polimeris Termomedegobis gazrdis problema
ukavSirdeba iseTi polimerebis sinTezis problemas, romelic jaWvSi ar Seicavs
naxSirbadis atomebs. axseniT ras efuZneba mecnierTa aseTi mosazreba.
organuli nivTierebebis umravlesoba kargad iwvis, rac ganpirobebulia maTi SedgenilobiT anu naxSirbadis SemcvelobiT. amasve ukavSirdeba polimeris Termomedegobis problemac. cxadia, Tu naxSirbadis atomebi jaWvSi ar iqneba, es imoqmedebs polimeris Termomedegobaze.
§25. element-organuli polimerebi
teqstis Semdeg
1. boWkos misaRebad iyeneben aminomJavebs, magaliTad ε-aminokapronmJavas,
Tumca iyeneben mxolod normaluri agebulebis aminomJavebs da ara maT izomerebs,
magaliTad
120
NH2 – CH2 – CH – CH2 – CH2 – COOH
|
CH3
axseniT, ra aris amis mizezi.
izomerebis gamoyenebisas makromolekulaSi iqneba ganStoebebi, rac Seamcirebs
molekulaTSoris moqmed Zalebs da polimeri naklebad mtkice iqneba.
2. praqtikaSi farTod gamoiyeneba boWko nitroni, romelic garegnulad gavs
Sals. is kargad inaxavs siTbos, gamoirCeva didi simtkiciT, elasturia, Termome­
degia. nitroni, yvela sxva bunebrivsa da qimiur boWkosTan SedarebiT, mdgradia
sinaTlisa da atmosferuli zemoqmedebis mimarT. misi monomeria akrilis mJavas
nitrili, anu akrilonitrili CH2 = CH – CN. SeadgineT nitrilis polimerizaciis
reaqciis toloba.
gamoyaviT monomeruli erTeuli.
nitrilis molekula CavweroT ase
CH2 = CH
|
CN
monomeruli erTeulebi iqneba _ CH2 _ CH _
|
CN
polimerizaciis reaqciis sqema iqneba
n
CH2 = CH →
|
CN
– CH2 – CH –
|
CN
n
3.
polipropilenis boWko gamoirCeva simsubuqiT. is wyalze msubuqia,
gamoirCeva agreTve didi simtkiciT, tuteebisa da mJavebis mimarT mdgradobiT.
gamoiyeneba sazRvao bagirebis, xaliCebis, TevzsaWeri badeebis, trikotaJis
nawarmis dasamzadeblad da sxva. SeadgineT propilenis polimerizaciis reaqciis
toloba.
propilenis formulaa CH3 – CH2 = CH2, CavweroT ase CH = CH2
|
CH3
monomeris formula iqneba _ CH_ CH2 _
|
CH3
polimerizaciis reaqciis sqemas ki eqneba aseTi saxe,.:
n
CH = CH2 →
|
CH3
– CH – CH2 –
|
CH3
n
4. Tu kauCuks 30%-ze met gogirds daamateben, miiReba xisti masala – eboniti,
romelic plastmasebis miRebamde erT-erT saukeTeso izolatorad miiCneoda. ro­
gor axsniT im faqts, rom eboniti aRar aris elastikuri?
TuU kauCuks imaze met gogirdis mivamatebT, vidre es saWiroa rezinis misaRebad,
vulkanizaciis dros wrfivi molekulebi Zalian bevrs adgilas aRmoCndeba erTmaneTTan `mikerebuli~, ris gamoc masala elastikurobas dakargavs da xisti gaxdeba _ es
aris eboniti.
121
5. suraTze Tqven xedavT mowyobilobas, romlis saSualebiTac mimdinareobs
kauCukis daSlis reaqcia. gaauferulebs Tu ara kauCukis daSlis produqti bro­
mian wyals? daasabuTeT Tqveni varaudi.
kauCukis daSlisas miiReba sawyisi monomeri, romelic dienuri naxSirwyalbadia, es
naerTi ki Seicavs ujer bmas, amitom bromiani wyali gauferuldeba.
6. TqvenTvis kargadaa nacnobi rezinis nakeTobani. imisaTvis, rom kauCukis
Tvisebebs gaecnoT, gaaSreT rezinis webo, romelic kauCukisa da benzinis narevia.
SeadareT rezinisa da kauCukis Tvisebebi, gamoikvlieT ra emarTeba maT gaTbobi­
sas.
rezini ufro elastikuria, vidre kauCuki, is kauCukze ufro mtkicea da temperaturis cvlilebisadmi ufro mdgradi. gacxelebisas kauCuki rbildeba da webvadi xdeba.
§ 26. biopolimerebi
1. gaecaniT Semajamebel sqemas `polimerebis klasifikacia~. SeadgineT mcire
ambavi sqemis mixedviT.
stereore­
gularuli
arastere­
ore­gu­laruli
bunebrivi
warmoSobis
mixedviT
stereoregula­
robis mixedviT
xelovnuri
sinTezuri
organuli
ZiriTadi jaWvis Sedgenilobis mixedviT
polimeri
element
organuli
araorganuli
wrfivi
makromolekulis formis mixedviT
ganStoebuli
sivrculi
gaxurebis mimarT
Termoplastikuri
damokidebulebiT
Termoreaqtiuli
miRebis xerxis mixedviT
polikondensaciis
polimerizaciis
polimeri warmoSobis mixedviT, SesaZloa iyos bunebrivi, xelovnuri da sinTezuri,
ZiriTadi jaWvis Sedgenilobis mixedviT arsebobs organuli (sadac ZiriTadi jaWvSi
naxSirbadatomebia), elementorganuli (sadac ZiriTad jaWvSi sxva elementebia, naSirbadis Semcveli radikalebi ki gverdiT jaWvSia, araorganuli, sadac naSirbadi
ZiriTad jaWvSi ar Sedis da arc organuli radikalebia). polimeri mikromolekulis
formis mixedviT SesaZloa iyos wrfivi, ganStoebuli da sivrculi, wrfivia magaliTad polieTileni, ganStoebulia saxamebeli, sivrculia rezini. arsebobis Termoplastikuri da Termoreaqtiuli polimerebi, Termoplastikuria magaliTad polie-
122
Tileni, kauCuki, Termoreaqtiulia fenoliformadehiduri fisi.
polimeri miiReba polimerizaciiis reaqciiT. am dros Tanauri produqti ar gamoiyofa, polimeri miiReba polikondensaciis reaqciiTac _ am dros Tanauri produqti
miiReba dabalmoklekuluri nivTierebis, magaliTad wylis saxiT. polimeri SesaZloa
iyos stereoregularuli da arastereoregularuli.
SeamowmeT^ Tqveni codna
1. erT-erT laboratoriaSi Seamowmes Zexvis nimuSSi saxameblis Semcveloba,.
risTvisac gamoiyenes kaliumis iodidis xsnari, radganac Seferiloba ar Seicvala,
`eqsperimentma~ daaskvnas, rom Zexvis nimuSSi saxamebeli ar aris, ras fiqrobT amis
Sesaxeb Tqven? ras urCevdiT eqsperiments?
saxameblis aRmomCenia Tavisufali iodi, da ara iodis romelime marili, amitom
kaliumis iodidiT saxameblis aRmoCena ver moxerxdeboda. saWiroa iodis xsnaris
gamoyeneba.
2. sqemaze mocemulia 1 t mSrali xis naxer­
xis gadamuSavebiT miRebuli masalebis saxeoba
da raodenoba.
_ SeiZleba Tu ara celulozas gada­
muSavebis process vuwodoT unarCeno war­
moeba?
daasabuTeT Tqveni mosazreba.
Tu Tqveni pasuxi dadebiTia, axseniT ra­
tom ar utoldeba produqtebis masaTa jami
nedleulis masas?
Tu produqtebis masa daxloebiT udris
nedleulis masas, maSin warmoeba unarCenoa.
70 + 350 + 80 + 5 + 44 + 50 = 599(kg) myari produqtebi
Tu am dros miRebuli siTxeebis moculobebs Sesabamis simkvriveze gadavamravlebT
da SevkrebT, miiReba daaxloebiT 300 kg produqti. e. i. sul daaxloebiT 900 kg.
miuxedavad imisa, rom aseTi toloba ar arsebobs, warmoeba unarCenod SeiZleba
CaiTvalos, zogan produqtebis miRebisas adgili aqvs samrewvlo danakargebs.
3. suraTze Tqven xedavT diagramas, romelic asaxavs adamianis organizmis qimi­
uri Sedgenilobas, gaiTvaliswineT Tqveni organizmis masa da daadgineT qimiuri
Sedgeniloba.
Tu magaliTad organizmis masaa daaxloebiT 60 kg, masSi iqneba wyali 65 · 60 ; cximebi
100
10 · 60
; cilebi 18 · 60 ; naxSirwylebi 5 · 60 ; sxva nivTiereba 2 · 60 .
100
100
100
100
4. suraTze gamosaxul cilis struqturebs Soris, romelia pirveladi, meoreuli
da mesameuli. daasabuTeT Tqveni varaudi.
(a) SemTxveva cilas pirveladi struqturaa, aq naCvenebia radikalebis, anu aminomJavebis naerTebis urTierTganlageba.
(b) SemTxveva cilis meoreuli struqturas aRwers, wyalbaduri bmebis warmoqmnis
cilis makromolekulebis calkeul ubnebs Soris.
(g) SemTxveva aRwers mesameuli struqturas, radgan mas spiralis forma aqvs.
123
danarTi
124
eTilenis hidrohalogenirebis Sesaxeb.
alkeni aseve urTierTqmedebs halogenwyalbadTan, ris Sedegadac miiReba monobromalkani,
magaliTad
CH3 _ CH =CH2 +HBr → CH3 _ CHBr _ CH3
propeni
2-brompropani
reaqcia mimdinareobs markovnikovis wesis Sesabamisad. `alkenTan halogenwyalbadis
mierTebisas wyalbadi uerTdeba ufro metad hidrirebul naxSirbadis atoms, anu im
naxSirbadatoms, romelTanac wyalbadis meti atomia. halogeni ki, uerTdeba naklebad
hidrirebuls~.
alkenis hidrohalogenirebis reaqcia ionuri reaqciaa. ionur reaqciebSi reagentis
molekula ionebad ixliCeba.
A :B → AA+ + :B–
ioni Tavisufali saxiT ar arsebobs da warmoqmnisTanave reaqciaSi Sedis aRebul
molekulasTan. kationi cdilobs SeiZinos eleqtronuli wyvili naxSirbadatomidan, xolo
anioni cdilobs Tavisi Warbi eleqtronuli wyvili gadasces naxSirbadatoms. ionebis
monawileobiT mimdinare reaqciebs ionuri reaqciebi ewodeba. ionuri reaqciebi or stadiad
mimdinareobs: jer kationi Sedis reaqciaSi da Semdeg anioni an piriqiT. Tu reaqciis pirvel
safexurze organul molekulas kationi daukavSirda, maSin igi naxSirbadatomidan ierTebs
eleqtronul wyvils da uerTdeba mas, xolo mezobel naxSirbadatoms Tavis muxts gadascems.
amgvarad warmoiqmneba organuli kationi, romelic reaqciis meore safexurze uerTdeba anions
da reaqciis produqtSi gadadis. ganvixiloT propilenTan bromwyalbadmJavas mierTeba.
(I stadia)
karbkationi
+
–
CH3 – CH – CH3 + Br → CH3 – CH – CH3
(II stadia)
Br
H-Br-is gaxleCis Sedegad warmoqmnili wyalbadis kationi uerTdeba ganapira CH2-is
naxSirbadatoms, risTvisac igi gamoiyenebs π-bmis eleqtronebs, xolo misi dadebiTi muxti
gadaecema mezobel naxSirbadatoms da warmoiqmneba organuli kationi-karbkationi, romelic
warmoqmnisTanave reaqciaSi Sedis Br–-is anionTan da warmoqmnis brompropanis molekulas.
125
mierTebis reaqcia alkadienTan
alkadeni ierTebs wyalbads, halogens., halogenwyalbads. mierTebis reaqcia pirobebis
mixedviT SeiZleba warimarTos rogorc 1 da 2, ise 1 da 4 mdebareobaSi.
Br
Br
CH2 = CH _ CH = CH2 +Br2→ CH2_ CH _ CH = CH2
an
Br
1,2 mierTeba
Br
CH2 = CH _ CH = CH2 +Br2→ CH2_ CH = CH _ CH2
1,4 mierTeba
divinilis molekulaSi naxSirbadis oTxive atomi sp2-hibridizaciaSia, ami­tom naxSirbadis
yvela atoms TiTo p-orbitali aqvs.
naxSirbadatomis p-orbitalebi erTmaneTs gverdulad gadafaravs orive mxridan da warmoqmnis saerTo (molekulur) orbitalebs, romlis saSualebiT oTxi π-eleqtroni Tanabrad
gadanawildeba molekulaSi. π-eleqtronebis aseT Tanabar gadanawilebas π-eleqtronebis delokalizacia ewodeba. xolo dienebs _ SeuRlebuli dienebi. aseTi delokalizaciis Sedegad
C – C da C = C bmis sigrZeebi TiTqmis gaTanabrebulia.
mierTebis reaqciebSi dienuri naxSirwyalbadis orive π-bma ixliCeba da oTxive naxSirbadatomTan gauwyvilebeli eleqtroni warmoiqmneba
CH2 = CH – CH = CH2 → [ CH2 – CH – CH – CH2 ]
miiReba Sualeduri nawilaki. Sualedur nawilakSi mezobeli (C-2 da C-3) naxSirbadatomebis
gauwyvilebeli eleqtroni erTmaneTs uwyvildeba da warmoqmnis π-bmas, xolo kidura naxSirbadatomebis (C-1 da C-4) eleqtronebi rCeba gauwyvilebeli saxiT. gauwyvilebeli eleqtroni erTi
Tavisufali valentobaa da moreagire nivTierebis atomebs ierTebs am eleqtronebis saSualebiT:
aseTi saxis mierTebis reaqciebs 1,4-mierTeba ewodeba. 1,4 mierTeba dienuri naxSirwyalbadebis ZiriTadi damaxasiaTebeli reaqciaa.
[CH2 – CH – CH – CH2 ]→ [ CH2 – CH = CH – CH2 ]
[CH2 – CH = CH – CH2 ] + Br – Br → CH2 – CH = CH – CH2
Br
Br
1,4-dibrombuteni
1,4 mierTebis Sedegad butadienidan miiReba ujeri naxSirwyalbadis halogennawarmi, romelic reaqciis meore safexurze kidev ierTebs bromis atomebs da warmoqmnis 1,2,3,4-tetrabrombutans.
126
benzolis bromirebis Sesaxeb
bromTan reaqciis SemTxvevaSi, Tu katalizatorad gamoyenebelia rkina (III)-is bromidi, SesaZlebelia benzolis birTvSi wyalbadis erTi atomis Canacvleba bromis atomiT.
C6H5Br + HBr
C6H6 + Br2
TiTqmis analogiuri meqanizmiT mimdinareobs benzolSi Canacvlebis reaqciebi
katalizatoris Tanaobisas. benzolis katalizuri bromireba ionuri meqanizmiT
mimdinareobs. katalizatoris gavleniT bromis molekula ionurad ixliCeba.
bromis kationi uerTdeba benzolis molekulis erT-erT naxSirbadatoms
π-bmis eleqtronuli wyviliT, xolo bromis dadebiTi muxti gadaecema mezobel
naxSirbadatoms
(I stadia)
benzoli
karbkationi
I stadiaze warmoqmnil karbkationSi 3π-bmisgan Sekruli, mdgradi eleq­tronuli
sistema (aromatuli seqsteti), romelic benzolis mdgradobas (dabal energetikul
mdgomareobas) ganapirobebda dairRva erTi π-bmis eleqtro­nebis ciklidan gamosvlis
gamo. miRebul kations aromatuli naerTebis damaxasiaTebeli Termodinamikuri
mdgradoba aRar aqvs. misi Sinagani energia gacilebiT didia benzolTan SedarebiT.
dabalenergetikuli mdgomareobis misaRwevad karbkationi cdilobs daibrunos
ciklSi mesame π-bma, rasac im SemTxvevaSi miaRwevs Tu bromian naxSirbadatomTan
arsebul wyalbadatoms Camoicilebs da dadebiT muxtsac gaatans. aseT SemTxvevaSi
ciklidan gasuli eleqtronuli wyvili ubrundeba isev cikls π-bmis saxiT.
+ H+
bromi ki rCeba benzolis naxSirbadatomTan dakavSirebuli. karbkationidan
moxleCili wyalbadis kationi uerTdeba bromis anions da HBr-is saxiT gamoiyofa
H+ + Br – → HBr↑
amrigad, benzolSi Canacvlebis reaqciebi mimdinareobs Semdegi sqemiT:
benzoli
karbkationi
brombenzoli
analogiuri meqanizmiT mimdinareobs benzolze HNO3, H2SO4 da sxva urTierT­
qmedeba.
127
aldehidebTan mierTebis reaqciis Sesaxeb
ormagi bmis polaruli xasiaTi aldehidebSi mierTebis sxva reaqciasac ganapirobebs, (wyalbadis mierTebis garda) magaliTad, wylis mierTebas, es gansakuTrebiT damaxasiaTebelia formaldehidisaTvis:
δ–
H
δ+
O
C
δ+
OH
δ–
‫ ׃‬OH
+H
H
O
С
OH
H
aq Semdeg movlenebs aqvs adgili: karbonilis jgufis naxSirbadatoms, romelsac
nawilobriv dadebiTi muxti aqvs, uerTdeba hidroqsilis jgufi Jangbadatomis
eleqtronuli wyvilis xarjze; p-bmis eleqtronuli wyvili gadadis karbonilis jgufis JangbadatomTan, misi meSveobiT am Jangbads uerTdeba protoni da warmoiqmneba
meore hidroqsilis jgufi. wyalxsnarSi formaldehidi upiratesad swored aseTi hidratuli formiT arsebobs (am Seqcevadi reaqciis wonasworoba Zlier aris gadaxrili marjvniv).
kuCerovis reaqciis Sesaxeb
dasawyisSi erTi p-bmis meSveobiT acetilens uerTdeba wyali da warmoiqmneba
vinilis spirti. magram ujeri spirtebi, romlebSic hidroqsilis jgufi ormagbmian
naxSirbadis atomTan aris dakavSirebuli, aramdgradia da advilad ganicdis izomerizacias. amitom vinilis spirti gardaiqmneba aldehidad:
OH
CH
CH + HOH
CH2
C
O
CH3
H
C
H
reaqcia adgilad ganxorcieldeba, Tu acetilens gavatarebT cxel wyalSi, romelic Seicavs gogirdmJavas da vercxliswyal(II)-is oqsids, ramdenime wuTis Semdeg
mimRebSi SeiZleba aRmovaCinoT aldehidis xsnari.
karbonmJavebis eleqtronuli agebulebis Sesaxeb
mJavebi spirtebisagan aRnagobis mixedviT imiT gansxvavdeba, rom maT molekulebSi wyalbadis ori atomis nacvlad Cndeba Jangbadatomi da swored karbonilSi Semavali Jangbadatomis gavleniT icvleba wyalbadatomis Tvisebebi hidroqsid-jgufSi,
C=O bmis (gansakuTrebiT p-bmis) eleqtronuli simkvrive gadanacvlebulia Jangbadisaken, rogorc ufro eleqtrouaryofiTi elementisaken. amis gamo karbonilis naxSirbadatomi iZens nawilobriv dadebiT muxts da misi kompensaciisaTvis izidavs hidroqsilis Jangbadatomis eleqtronebs. am Jangbadatomze eleqtronuli simkvrive
mcirdeba da amitom is Tavisken gadawevs O-H bmis eleqtronul simkvrives. hidroqsilis jgufSi bmis polaroba izrdeba da wyalbadi protonis saxiT ufro advilad wydeba, eleqtronebis am wanacvlebas formulaSi gamosaxaven isrebiT:
O
R
128
C
O
H
testebis pasuxebi
ki
eb
ia
r
xv
T
va
1
2
3
4
5
6
7
8
9
10
eb
nt
i
Temis
dasaxeleba
i
alkanebi
I
3
3
b
1,4
4
3
4
4
1
4
cikloal­
II
2
4
4
4
3
4
4
4
3
4
I
4
2
b
2
4
2
3
4
2
4
II
3
3
d
4
3
4
4
2
4
1
I
4
2
1
3
4
3
3
3
4
1
II
3
3
4
3
4
4
3
4
4
2
I
2
3
4
2
1
3
1
1
2
4
II
1
2
2
3
1
2
3
4
4
3
I
4
2
4
2
3
4
2
2
4
1
II
4
2
4
2
4
3
4
3
4
2
I
3
4
2
4
3
4
3
4
4
3
II
3
3
1
1
4
2
3
1
1
2
I
2
1
3
2
4
4
3
2
4
3
II
3
3
3
4
1
4
2
3
4
1
I
kanebi
alkenebi
II
alkinebi
alkadienebi
III
arenebi
spirtebi
IV
fenolebi
aldehidebi
V
karbonmJa­
vebi
esterebi
VI
naxSir­
wylebi
aminebi
VII
aminomJa­
vebi
129