?aoa?ao ii
I?aaie/aneie oeiee.
oaia:
«?aaeoeee yeaeo?ioeeueiiai caiauaiey a a?iiaoe/aneii ?yaeo»
Iaeaaeaiea:
Yeaeo?ioeeueiia caiauaiea a aaicieueiii eieueoea
2
I?aaeea i?eaioaoeee yeaeo?ioeeueiiai caiauaiey a aaicieueiii eieueoea
4
?aaeoeey O?eaeaea-E?aoona 8
Aaeiaaie?iaaiea 10
Noeueoe?iaaiea 11
Ieo?iaaiea 13
Yeaeo?ioeeueiia caiauaiea a aaicieueiii eieueoea.
A ?aaeoeeyo yeaeo?ioeeueiiai caiauaiey a aaicieueiii eieueoea aoii
aiaei?iaea caiauaaony ia yeaeo?ioeeueiue ?aaaaio i?e nio?aiaiee
a?iiaoe/aneiai oa?aeoa?a enoiaeiiai niaaeeiaiey:
.
Iaoaieci yeaeo?ioeeueiiai caiauaiey iiaeii caienaoue oae:
.
1-y noaaeey: ia?aciaaiea i-eiiieaena. A yoii neo/aa ia?acoaony neaaay
naycue iaaeaeo i-yeaeo?iiiui iaeaeii aaicieueiiai eieueoea e
yeaeo?ioeeueiui ?aaaaioii n aeaoeoeeoii yeaeo?iiiie ieioiinoe i?e
nio?aiaiee a?iiaoe/aneiai naenoaoa. Yeaeo?ioeeueiue ?aaaaio
?aniieaaaaony iau/ii ia?iaiaeeeoey?ii ieineinoe eieueoea aaeieue aai ine
neiiao?ee. Yoa noaaeey i?ioaeaao auno?i e ia aeeyao ia nei?inoue
?aaeoeee. Nouanoaiaaiea i-eiiieaena aeieacuaaaony iaoiaeii
OO-niao?ineiiee.
.
2-y noaaeey: ia?aciaaiea a-eiiieaena. Yoa noaaeey iaaeeaiiay e
i?aeoe/anee ia ia?aoeiay. Ia?acoaony eiaaeaioiay a-naycue iaaeaeo
yeaeo?ioeeii e aoiiii oaea?iaea aaicieueiiai eieueoea, i?e yoii aoii
oaea?iaea ia?aoiaeeo ec sp? a sp?-aaeaioiia ninoiyiea n ia?ooaieai
a?iiaoe/aneiai naenoaoa e ia?aciaaieai oeeeeiaaenaaeeaieeueiiai eaoeiia
(eiia aaicieaiey). Eaoeii aaicieaiey aianoa n i?ioeaieiiii ia?acotho
eiiiia niaaeeiaiea, oi?ioi i?iaiaeyuaa yeaeo?e/aneee oie. A eiia
aaicieaiey ana aoiiu oaea?iaea ?aniieiaeaiu a iaeiie ieineinoe, a
caianoeoaee o sp?-aea?eaeeciaaiiiai aoiia oaea?iaea ia?iaiaeeeoey?ii ae.
.
Yeaeo?ioeeueiue ?aaaaio i?eniaaeeiyaony ca n/ao aeaoo yeaeo?iiia
i-yeaeo?iiiiai iaeaea aaicieueiiai eieueoea n ia?ooaieai a?iiaoe/aneiai
naenoaoa. Onoie/eainoue oeeeeiaaenaaeeaieeueiiai eaoeiia iaoneiaeaia
aeaeieaeecaoeeae iieiaeeoaeueiiai ca?yaea n ia?aciaaieai iaciia?iie
/anoeoeu, a eioi?ie /aou?a i-yeaeo-?iia aeaeieaeeciaaiu a iiea iyoe
yaea?.
Enoeiiia no?iaiea eiia aaicieaiey i?iiaaeooi/iia iaaeaeo o?aiy
i?aaeaeueiuie no?oeoo?aie, ?aaeueii ia nouanoaothueie (i,?-nii?yaeaiea),
iieiaeeoaeueiue ca?yae eieaeeciaai i?aeiouanoaaiii a i- e i-iieiaeaieyo
e ianoo i?eniaaeeiaiey yeaeo?ioeea.
I?eaeaeueiua no?oeoo?u a-eiiieaena:
.
Iacioi?ioeu:
.
Aaicieaieaaua eiiu iaei onoie/eau e auniei?aaeoeeiiiu, ii nouanoaotho
aeeeoaeueiia a?aiy a neeueiie eeneioa eee neeueiieeneie n?aaea, aaea
i?ioeaieii ia iaeaaeaao ioeeaioeeueiuie naienoaaie e ia aoaeao
iouaieyoue i?ioii.
3-y e 4-y noaaeee: ia?aciaaiea aoi?iai i-eiiieaena e a?iiaoecaoeey.
a-eiiieaen iiaeao i?aa?auaoueny a iiaue iaei onoie/eaue i-eiiieaen,
eioi?ue iiae aicaeaenoaeai iniiaaiey, iau/ii i?ioeaieiia,
aeai?ioiie?oaony. I?e yoii ainnoaiaaeeaaaony a?iiaoe/aneay nenoaia: aoii
oaea?iaea ia?aoiaeeo ec sp? a sp?-aaeaioiia ninoiyiea e caiueaaony
a?iiaoe/aneee naenoao.
.
a-eiiieaen i-eiiieaen
.
Ia?aua aeaa noaaeee yeaeo?ioeeueiiai caiauaiey o a?iiaoe/aneeo
niaaeeiaiee aiaeiae/iu yeaeo?ioeeueiiio i?eniaaeeiaieth e aeeaiai, a 3-y
e 4-y noaaeee ioee/athony. Aianoi i?eniaaeeiaiey ioeeaioeeueiiai
?aaaaioa e ea?aieaoeiio iouaieyaony i?ioii. Oae eae ia?acoaony
yia?aaoe/anee aieaa onoie/eaay a?iiaoe/aneay nenoaia (1) ii n?aaiaieth n
aeeaiiaie (2):
.
I?aaeea i?eaioaoeee yeaeo?ioeeueiiai caiauaiey a aaicieueiii eieueoea.
Ana caianoeoaee aeaeyony ia aeaa oeia: ia?aiai ?iaea (i- e
i-i?eaioaiou) e aoi?iai ?iaea (i-i?eaioaiou).
.
Caianoeoaee ia?aiai ?iaea, e?iia Alk-a?oiiu, aieaa
yeaeo?iio?eoeaoaeueiu, /ai oaea?iae, iiyoiio iie oiaiueoatho
yeaeo?iiioth ieioiinoue eieueoea ii iaoaiecio io?eoeaoaeueiiai
eiaeoeoeaiiai yooaeoa (-I-yooaeo). Iaeiaei a aieueoeinoaa caianoeoaeae
ia?aiai ?iaea aoii, naycaiiue n aaicieueiui eieueoei, eiaao
iaiiaeaeaiioth ia?o yeaeo?iiia, niiniaioth anooiaoue a ?,i-nii?yaeaiea
(+I-yooaeo). Ioiineoaeueiay neea -I e +I-yooaeoia e ii?aaeaeyao
?aaeoeeiiioth niiniaiinoue niaaeeiaiey.
Caianoeoaee aoi?iai ?iaea aieaa yeaeo?iio?eoeaoaeueiu, /ai oaea?iae
(-I-yooaeo) e, e?iia NR -a?oiiu, eiatho i-nayce, niiniaiua anooiaoue a
nii?yaeaiea n aaicieueiui eieueoeii.
I?oi-, ia?a-i?eaioaiou Iaoa-i?eaioaiou
Aeoeae?othuea:
-O
-NH(, -NHR, -NR(
-OH, -OR
-NHCOR
-SH, -SR
-Alk, -A/
Aeacaeoeae?othuea:
-F, -Cl, -B/, -I Aeacaeoeae?othuea
-NR(
-NO(
-SO(H
-COR
-CHO
-COOH, -COOR
-CN
-CCl(
-CF(
-CH(NO( e ae?.
Iaeioi?ua aeeeeueiua a?oiiu, ianouea yeaeo?iiiaeoeaioi?iua caianoeoaee,
yaeythony i-i?eaioaioaie e aeacaeoeae?otho eieueoei. Yeaeo?ioeeueiue
?aaaaio a oaeeo niaaeeiaieyo i?aeiouanoaaiii anooiaao a i-iieiaeaiey.
Oaeeie caianoeoaeyie yaeythony:
Nouanoaotho aeaa iaoiaea aeey ii?aaeaeaiey ?aaeoeeiiiie niiniaiinoe
niaaeeiaiee e ianoa i?aeiouanoaaiiiai anooieaiey a eieueoei:
noaoenoe/aneee e aeeiaie/aneee.
1.Noaoenoe/aneee iiaeoiae – iniiaai ia o/?oa iieiaeaiey: yeaeo?ioeeueiue
?aaaaio, iaeaaeathuee aeaoeoeeoii yeaeo?iiiie ieioiinoe, aoaeao
i?aeiouanoaaiii aoaeiaaoue oa iieiaeaiey eieueoea, aaea yeaeo?iiiay
ieioiinoue iaeneiaeueia.
i,i-i?eaioaiou: anee a eieueoea i?enoonoaoao caianoeoaeue n
iaiiaeae?iiie yeaeo?iiiie ia?ie, aeey eioi?iai +I-yooaeo (?,i-) aieueoa
-I-yooaeoa, oiaaea ana iieiaeaiey eieueoea eiatho iiauoaiioth
yeaeo?iiioth ieioiinoue ii n?aaiaieth n aaicieii. ?aaeoeeiiiay
ieioiinoue oaeiai niaaeeiaiey auoa iacaiau?iiiai aaiciea. Iaeaieueoee
ecauoi/iue ca?yae nin?aaeioa/eaaaony a i- e i-iieiaeaieyo e
caianoeoaeth, eoaea e anooiaao i?aeiouanoaaiii yeaeo?ioeeueiue ?aaaaio.
.
i-i?eaioaiou oiaiueoatho yeaeo?iiioth ieioiinoue eieueoea, ii iniaaiii
neeueii a i- e i-iieiaeaieyo. Iiyoiio i?aeiouanoaaiii yeaeo?ioeeueiue
?aaaaio anooiaao a i-iieiaeaiey, auae?ay ianoa iaeiaiueoae
aeacaeoeaaoeee.
.
2.Aeeiaie/aneee iiaeoiae. ?acee/ea a aeaenoaee i?eaioaioia yaeyaony
neaaenoaeai eo aeeyiey ia noaaeeueiinoue ia?acothuaainy a i?iiaaeooi/iie
noaaeee aaicieaieaaiai eiia (a-eiiieaena). *ai auoa onoie/eainoue
eioa?iaaeeaoa, oai iaiueoa yia?aey aeoeaaoeee.
i,i-i?eaioaiou. I?eaioaoeey a i- e i-iieiaeaiey e caianoeoaeth ia?aiai
?iaea i?aaeii/oeoaeueiaa, a-eiiieaen aieaa onoie/ea aneaaenoaee neeueii
aeaeieaeecaoeee ca?yaea 6 a aeaeieaeecaoeee ca?yaea i?eieiaao o/anoea
a?oiia II. Niioaaonoaaiii oiaiueoaaony naiaiaeiay yia?aey aeoeaaoeee
ia?aoiaeiiai ninoiyiey a noaaeee ia?aciaaiey a-eiiieaena. A neo/aa
anooieaiey yeaeo?ioeea a i-iieiaeaiea noaaeeecaoeey ca n/?o a?oiiu II
iaaaeeea.
.
i-i?eaioaiou. Aiaeec i?aaeaeueiuo no?oeoo? a-eiiieaenia iieacuaaao, /oi
aoi?ie caianoeoaeue aoaeao i?aeiouanoaaiii anooiaoue a i-iieiaeaiea e
caianoeoaeth aoi?iai ?iaea. Iioiio /oi oieueei a yoii neo/aa
caianoeoaeue ia aoaeao iaoaoue aeaeieaeecaoeee iieiaeeoaeueiiai ca?yaea
a o?ao iiceoeeyo eieueoea a-eiiieaena. Ia?aciaaiea a-eiiieaena n
iieiaeaieai yeaeo?ioeea a i- e i-iieiaeaieyo iaei aa?iyoii, oae eae
iieiaeeoaeueiue ca?yae eieaeeciaai eeoue a aeaoo iieiaeaieyo eieueoea.
.
I?aaeea i?eaioaoeee eiatho ioiineoaeueiue oa?aeoa? e oeacuaatho eeoue
ia i?aeiouanoaaiiia ianoi anooieaiey aoi?iai caianoeoaey. *aua anaai
ia?acothony ana o?e eciia?a a oii eee eiii niioiioaiee.
I?eaioaoeey a aeecaiau?iiuo i?iecaiaeiuo aaiciea.
Anee a eieueoea oaea anoue aeaa caianoeoaey, oi ?aaeoeeiiiay
niiniaiinoue e ianoi anooieaiey o?aoueaaicaianoeoaey ii?aaeaeyaony
?ani?aaeaeaieai yeaeo?iiiie ieioiinoe a eieueoea n o/?oii eo I- e
I-yooaeoia. Aeaenoaeth yeaeo?ioeea iiaeaa?aeaiu iieiaeaiey n iaeaieueoae
yeaeo?iiiie ieioiinoueth eee i?eaiaeyuea e iaeaieaa onoie/eaiio
a-eiiieaeno.
A eieueoea aeaa caianoeoaey iaeiiai ?iaea:
a) Aeaa i, i-i?eaioaioa. A yoii neo/aa iaeaieueoay ?aaeoeeiiiay
niiniaiinoue iaaethaeaaony o niaaeeiaiee n i-iieiaeaieai caianoeoaey
(niaeaniaaiiay i?eaioaoeey).
a) Aeaa i-i?eaioaioa. Oaeea niaaeeiaiey i?iyaeytho ieceoth
?aaeoeeiiioth niiniaiinoue, iaeiaei ec o??o eciia?ia iaeaieueooth
aeoeaiinoue i?iyaeytho i-eciia?u (niaeaniaaiiay i?eaioaoeey).
?aaeoeey O?eaeaey-E?aoona.
?aaeoeey O?eaeaey-E?aoona – aeeeee?iaaiea eee aoeeee?iaaiea
a?iiaoe/aneeo niaaeeiaiee a i?enoonoaee eaoaeecaoi?ia – eeneio Euethena
(AlCl(, BF(, FeCl() eee ieia?aeueiuo eeneio (HF, H(PO( e ae?.). A
ea/anoaa aeeeee?othueo n?aaenoa eniieuecothony aeeeeaaeiaaieaeua aeeaiu
e nie?ou, a a ea/anoaa aoeeee?othueo – aoeeeaaeiaaieaeu:
Aeeeee?iaaiea:
Aoeeee?iaaiea:
Aeeeee?iaaiea:
Aeeeeaaeiaaieaeu iaeaieaa ?ani?ino?aiaiiua aeeeee?othuea n?aaenoaa.
Ia?aciaaiea yeaeo?ioeeueiiai ?aaaaioa: oeaio?aeueiue aoii eaoaeecaoi?a
ia?acoao a-eiiieaen, a eioi?ii naycue oaea?iae – aaeiaai neeueii
ineaaeaia e eaaei ?ac?uaaaony n ia?aciaaieai eiiiie ia?u:
CH(-CH(-Cl + AlCl( [CH(CH(-Cl-AlCl(] CH(CH( + AlCl(
Aeoeaiinoue aeeeeaaeiaaieaeia oiaiueoaaony a ?yaeo: AlkF > AlkCl > >
AlkB/ > AlkI (a ii?yaeea oiaiueoaiey n?iaenoaa aaeiaaia e aoiio
aethieiey). Ia aeoeaiinoue aeeeeaaeiaaieaeia aeeyao no?iaiea aeeeeueiie
oeaii/ee: o?aoe/iua aieaa aeoeaiu, /ai aoi?e/iua, eioi?ua aeoeaiaa
ia?ae/iuo, yoi iaoneiaeaii onoie/eainoueth ia?acothueony ea?aieaoeiiia.
?aaeoeey yeaeo?ioeeueiiai caiauaiey ia?aoeia:
.
?aaeoeeae O?eaeaey-E?aoona i?eaiaeeo e ia?aciaaieth eciia?ia. Iai?eia?,
aeeeee?iaaiea aaiciea i-i?iieeoei?eaeii i?eaiaeeo e ia?aciaaieth 70%
ecii?iieeaaiciea (eoiiea):
C(H( + CH(CH(CH(Cl C(H(-CH-CH( + C(H(CH(CH(CH(
70% CH(
30%
Yoi iiaeii iauynieoue ia?aa?oiie?iaeie ia?ae/iiai i-i?iieeueiiai
eaoeiia a ecii?iieeueiue:
H
CH(CH(CH(-Cl-AlCl( [CH(-CH-CH( CH(-CH-CH(] AlCl(
Aeeaiu e nie?ou oae aea oe?iei eniieuecothony a ?aaeoeeyo
O?eaeaey-E?aoona. Iai?eia?, aeey iieo/aiea eoiiea i?eiaiytho i?iieeai:
CH(
C(H( + CH(=CH-CH( C(H(-CH-CH(
Aeeeee?iaaiea eae?o, anee aaeiaaieae aethieiey niaea?aeeo neaaeu
aaeiaaiiaiaei?iaea (nieaoaeecaoi?a):
HX + AlX( H [AlX(]
CH(CH=CH( + H [AlX(] [CH(-CH-CH(] AlX(
Aeeaiu anooiatho a ?aaeoeeth aeeeee?iaaiey e a i?enoonoaee ieia?aeueiuo
eeneio (HF eee H(PO():
CH(-CH=CH( + H(PO( [CH(-CH-CH(] H(PO(
Nie?ou oiaea o/anoaotho a aeeeee?iaaiee a i?enoonoaee eeneio Euethena
eee ieia?aeueiuo eeneio:
R-O + BF( R [HOBF(]
H
A ?aaeoeeth O?eaeaey-E?aoona anooiatho e aeeeeueiua i?iecaiaeiua
aaiciea. ?aaeoeey ianaeaeoeaia% e?iia iiiiaeeeee?iaaiiiai niaaeeiaiey
ia?acoaony aee- e iieeaeeeecaiau?iiua:
Iiiiaeeeecaiaiu?iiua aieaa ?aaeoeeiiiiniiniaiu, /ai aaicie (Alk-a?oiia –
caianoeoaeue ia?aiai ?iaea), e eaa/a anooiatho a ?aaeoeee
yeaeo?ioeeueiiai caiauaiey. ?aaeoeey O?eaeaey-E?aoona ia?aoeia, i?e
iaa?aaaiee i?ienoiaeeo ia?aa?oiie?iaea i- e i-aeeaeeeeaaicieia a
oa?ie/anee aieaa onoie/eaue i-aeeaeeeaaicie. A ?aaeoeeth
O?eaeaey-E?aoona ia anooiatho niaaeeiaiey n caianoeoaeyie aoi?iai ?iaea,
aeacaeoeae?othueie eieueoei.
Aaeiaaie?iaaiea.
1.Oei?e?iaaiea aaiciea: ?aaeoeey yecioa?ie/aneay , ii yoiio aaaaeaiea
aaeiaaia inouanoaeyaony a i?enoonoaee eaoaeecaoi?a (eeneio Euethena) a
aeeaeeie oaca, aac iaa?aaaiey. Iaeaieaa /anoi eniieuecotho oei?eae
aeaeaca (III).
2Fe + 3Cl( 2FeCl(
Cl-Cl + FeCl( Cl Cl FeCl( Cl-Cl-FeCl( [ Cl
][FeCl(]
?aaeoeey i?ioaeaao a eia?oiii ?anoai?eoaea.
Aaicieueiia eieueoei aoaeoaony iaeiiece?iaaiiui eiiieaenii, a ?ac?ua
nayce Hal-Hal eae?o ia noaaeee ia?aciaaiey aaicieaieaaiai eaoeiia.
Ionoonoaea ecioiiiiai yooaeoa oeacuaaao ia oi, /oi noaaeey ia?aciaaiey
a-eiiieaena naiay iaaeeaiiay noaaeey i?ioeanna.
I?e ecauoea oei?a oei?e?iaaiea iiaeao i?ioiaeeoue ii nooiai/aoie noaia.
Aianoa n oei?aaicieii ia?acoaony i- e i-aeeoei?aaicieu.
Noeueoe?iaaiea.
A ea/anoaa ?aaaaioia i?e noeueoe?iaaiee eniieuecoaony na?iay eeneioa e
ieaoi. Noeueoe?iaaiea ia?aoeii e iiaeao nii?iaiaeaeaoueny ia?aciaaieai
i?iaeoeoia aoi?e/iiai caiauaiey – aeea?eenoeueoiia:
A/-H + HOSO(OH A/SO OH + H(O
A/SO(OH + HA/ A/SO(A/ + H(O
Noeueoii ia ia?acoaony i?e ecauoea na?iie eeneiou, ecauoie na?iie
eeneiou eniieuecotho iioiio, /oi i?e oiaiueoaiee a? eiioeaio?aoeee ?acei
oiaiueoaaony nei?inoue noeueoe?iaaiey, ia/eiaao i?aiaeaaeaoue ia?aoiay
?aaeoeey – aeae?ieec.
A ea/anoaa noeueoe?othuaai ?aaaaioa iiaeao aunooiaoue ieneae na?u (YI).
Ia?aciaaiea ieneaea na?u (YI) iiaeao i?ienoiaeeoue a ?acoeueoaoa
aaoii?ioieeca na?iie eeneiou:
H
HOSO(OH + H-OSO(OH HOSO(O-H + OSO(OH
HOSO(O-H H(O + HOS H(O + S
H
O
Aunieay yeaeo?ioeeueiinoue na?u iaoneiaeaia aunieie iiey?iinoueth nayca
S-O. Yoi i?eaiaeeo e oiio, /oi a noaaeee ia?aciaaiey a-eiiieaena o na?u
inaiaiaeaeaaony naiaiaeiay i?aeoaeue, niiniaiay ia?aciaaoue a-naycue n
aeaoiy i-yeaeo?iiaie eieueoea.
Noeueoe?iaaiea:
.
I?e noeueoe?iaaiee ana noaaeee i?ioeanna ia?aoeiu. A neo/aa
noeueoe?iaaiey ieaoiii, a eioi?ii iao neeueiiai iniiaaiey – aiaeu,
niinianoaothuaai iouaieaieth i?ioiia io a-eiiieaena, nei?inoue
ii?aaeaeyaony noaaeeae iouaieaiey i?ioiia, i?enoonoaoao ecioiiiue
yooaeo. Anee noeueoe?otho eoii?iniui ianeii, a eioi?ii anoue aiaea, oi
naiie iaaeeaiiie yaeyaony noaaeey ia?aciaaiey a-eiiieaena, ecioiiiue
yooaeo ionoonoaoao.
Ieo?iaaiea.
Ieo?iaaiea iiaeao i?ienoiaeeoue iiae aeaenoaeai ?aciuo ieo?othueo
?aaaaioia: eiioeaio?e?iaaiiie eee ?acaaaeaiiie acioiie eeneiou;
ieo?othuae niane (niane acioiie e na?iie eeneio); niane ieo?aoa eaeey e
na?iie eeneiou: KNO( + H(SO( KHSO( + HNO(; niane acioiie
eeneiou n oenoniui aiaeae?eaeii:
O O O
CH(-C-O-C-CH( + HO:NO( CH(-C-O-NO( (aoeaoeeieo?ao)
Yeaeo?ioeeueioth aoaeo aaicieueiiai eieueoea inouanoaeyao
ieo?iiee-eaoeii, ia?acothueeny ec ieo?othuae niane:
HNO( + 2H(SO( NO( + H(O + 2HSO(
Ieo?iaaiea i?ienoiaeeo ii iau/iiio iaoaiecio, ecioiiiue yooaeo
ionoonoaoao:
Eaoeii ieo?iiey, aoiiu acioa iaoiaeyony a sp-aea?eaeecaoeee, ia
niaea?aeeo naiaiaeiuo i?aeoaeae. A i-eiiieaena ii ?aniieaaaaony aaeieue
ine neiiao?ee aaicieueiiai eieueoea, nio?aiyy sp-aea?eaeecaoeeth. A
noaaeee a-eiiieaena aoii acioa ia?aoiaeeo a sp(-aea?eaeecaoeeth.
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