SN1 / SN2

1
9?
????????????? ???
E1 / E2
??????
????
SN1 / SN2
2
9?1 ????????????????????
????????????????????
LDA
???
???
???
3
???????????????????H??????
4
???
?
?
gt
gt
gt
????
E2
5
9?2 ????????????????????? ?????????????????????
?????????HX??????????????????????
????????????? (alkyloxonium ion)
?
SN2
SN2
?
?????????HCl ??????????????!!
?
6
???????????????,??????????????????? SN1???E1??
????? ?????
??
????????????? (alkyloxonium ion)
????
7
???????????????,???,????????
hyperconjugation
?????????
C
CH
(tert-???????)
??????????????
(???)
(???)
(???)
???????
???????
??????????
tert-???????
8
????
?????
??
E1
9
?????
??????
10
9?3 ????????????
?????????SN1??????
??????HBr?SN1??????????(hydride shift)
????
????
?????????
??????????
??????????
lt??
11
?????????????????


12
??????????????????????????
??????????????????????????
13
??????????E1??
???????????
14
????????????????????
??????????
??????????
CH3?????????? alkyl shift (alkyl group migration)
15
???????????????????
??????
??????????(???)
16
9?4 ???????????????????????
17
?????(esterification)
???????????????????????
???
??1
??2
18
????
???
????
???????
??1
??2
19
?????????
Nu
20
??????????????
??????????,???????????????????? ??????????????,???
????????????? ???????
21
9?5 ?????????????
?????,IUPAC????? ?????????????
??????? (methoxyethane)
?????????? (ethyl methyl ether) ???
2??????2????????? (2-ethoxy-2-methylpropane)
cis?1??????2???????????? (cis-1-ethoxy-2-methoxycy
clopentane)
???????????
22
??????????
???????????
????? heteroatom
?????????? (oxacyclopentane) ?????(oxolane) ??????
??? (THF)
?????????? (oxacyclohexane) ????(oxane) ?????????
(tetrahydropyran)
????????? (oxacyclobutane) ?????(oxetane)
?????????? (oxacyclopropane ) ?????(oxirane) ?????
(epoxide ) ???????? (ethyleneoxide)
???(furan)
???(pyran)
???????(heterocyclic compound) ?????????????(oxa
cycloalkane)????? ???????(oxa)???????????????? ??
???????
23
??????(cryptand)

???????? (cryptate)
????? Ionophore ?????? Ion transport agent
???????? tetrodotoxin
????? monensin
24
9?6 Williamson???????
?????,SN2 ????????
CH3(CH2)3ONa CH3(CH2)3Cl
CH3(CH2)3O (CH2)3CH3
DMSO
?
25
???????,??? SN2 ?????
26
?????????????????
3 gt 5 gt 6 gt 4 gt 7 gt 8
DG DH TDS
DH ????? ? ???? 6gt5,7,8gt4gt3 ? ???? 3gtgt
6,5,4,7,8 DS ????? ? ?????????????? DS ?
?????????(?????) 3gt4 gt 5 gt 6 gt 7gt8
E
DG
????
27
??? Williamson ???????,?????
28
9?7 ???????????????????
???????????
????
???
29
SN1?
????
?????????
???????
86
??????