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(1)???? (2)???? (3)?????

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Title: Author: USER Last modified by: USER Created Date: 9/19/2002 6:47:29 AM Document presentation format: – PowerPoint PPT presentation

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Title: (1)???? (2)???? (3)?????


1
??? ??????
  • ????????????????????????????????
  • (1)???? (2)???? (3)????? 
  • ??????
  • (A)???? ?????
  • (B)???? ??????
  • (C)????? ?????
  • (D)????? ??????

2
SN1?????????
  • ?????????????????????????????????,???????????????(
    ????)???

3
  • ???????,??????????????
  • ?????????????????????????
  • ?????????????,???????,?????????????

4
A. ??????????????
  • ???????????,???????????,??X?????????,???????????
    ??????????A???????????????????,??????????????
  • ????????????,?????????,?X????????,?????????????
    ????????,??????????????????

5
????????,??????????????
6
  • ????(I)?(II)??,?????(I) ???????????,??????????????
    ??????,?????????,??????????,?????????

7
  • B. ????????????
  • ??????????,R?????????????,???????X????,??????????
    ,??????????
  • ????,?????????????X?????R??????,????????????????

8
  • ???()
    ??()
  • 80????? 98 2
  • 60????? 95 5
  • ? ? 83 17
  • SN1???????
  • ?SN1?????,????????????,????????????,?????????,
    ????????????,??????????????????????,??????????

9
SN1?????????
  • (I)??????(II)????????,????????????????????????(I
    II)???????,???????????????????????????????????,???
    ??????????????????????????????R?X-?????????,?????
    ??????

10
(No Transcript)
11
  • (a)SH????RX?SR(????),?????SN2???
  • (b)?????????,?????????,???(A)???????????,???(A)?(B
    )??,????????????
  • (c)???????????,??????????,????????,???????????,???
    ?????(d)????(1-d)?
  • (d)????R,?????,SH??????????,????????

12
SN2??????
  • ?SN2????????????,????,????(I)???????????(II)??????
    ?

13
  • C-A??????C-X?????,???????,?????,C-X????????????C-A
    ??????????????SP3???????SP2????,??P???????????A??,
    ??????????????

14
?????????????
  • ?????????????????,???RX???R?X???(?????????)??????
    ????????(??,????)

15
R?????
  • (a)???????????????,?
  • Z??????????,SN1??????,a-????????????Z??????????,?
    SN1??????,Z???????????????,????????
  • (b)??a?????????????
  • ??SN1?SN2 ????????

16
  • ???????SP??????SP2??????????,?????????,??????????
    ???????????????,??SP3??????????SP2??????SP????????
    ????????????
  • ?????????????????,?????????????????????????,?????
    ?????????????CX?,???CX??????????CX???????

17
  • (c) ß??????, ?ß?????,??????????SN1?SN2???????.
  • ?SN1???????????????????.
  • ?SN2???????P???(?????????????)???p??????SN2???????
    ??.

18
R?????
  • a?ß????,?SN2???????,?SN1???????.
    ?SN2????????,???????SN2????SN1?.
  • ? RBr??????????
  • R CH3 C2H5 i-C3H7 t-C4H9
  • K 100 1.65 0.022 0.0048

19
  • ?SN1??,???????????????????????????
  • ??????gt??????gt??????
  • ??, ????????,?????????????,?????.
    ß?????SN1???????????
  • ??????????????

20
?????
  • ?SN2?SN1??????????,?SN2???,??????????????????????.
    ??SN1?????,??????????????????.

21
(3)????????
  • (a) ???????????(????????)??,?RX???????,
    ???SN1??????, ??????????.????SN2??????.
  • ?1-??????????????????
  • ? ? ? ? k?? ?
    ? ? ? k??
  • CF3SO3-
    1.4108 CF3CO2-
    2.1
  • p-???????? 4.4105 Cl-
    1.0
  • p-??????? 3.7104 F-
    910-6
  • CH3SO3- 3.0104
    p-???????? 5.510-6
  • I-
    91 CH3CO2-
    1.410-6
  • Br-
    14 

22
  • (b) ??????????????
  • I-gtBr- gtCl- gtF-
  • ??C-X???????????,?????????????????????????????????
    ?
  • (c)  ?????????????????????,?????????????????????,
    ???SN1??.
  • ? RX?80??????????????/???????
  • R ?? ?? ??? ??? 1-????
  • kOTs/kBr 11 10 40 4000
    9750

23
(4) ??????????
  • (a) ?????????
  • ???????????SN1?????????, ??SN1??????????????,
    ???????????.
  • ??????SN2?????????,??????????,?SN2??????.

24
(b) ?????????????????
  • ????????, ?SN2????????

25
(5) ?????
  • (a) ???????
  • ??RX?????????SN1?? ?C6H5-Cl?????, ??????SN1????,
    ?????SN2??.
  • (b)   ????????????

26
4.???????????
  • ?????(Walden)
  • ?????????????????????????????,?????????

27
5. ????
  • ???????????????????????????????,???????????,??????
    ???????????????????,?????????,????????????(Neighbo
    ring group participation)?
  • ????????????????????????????????

28
????
  • ????????????????,???????????????
  • ?????????????
  • ??????????????? ???-?????????????p??????C-C?C-Hs?
    ?????n?????p?????s????.

29
(a) n????
  • ?????????????????????????ß??????,?????????????????
  • COO-(???COOH)?OCOR?COOR?COAr?OR?OH?O-?NH2?NHR?NR2?
    NHCOR?SH?SR?S-?Br?I?Cl (IgtBrgtCl)

30
????SN2??, ????????
  • ???
  • ???
  • ??????,??, ???Nu??????????????,???Z?????????,?????
    ??????
  • ???????????????,?????Z????Nu????,???S??????

31
  • ???3-?-2-?????(Threo)????()?HBr???,??????()-2,3
    -????

32
  • ??????????????????I gt Br gt Cl,???????????????????
    ???F?????,??????,??????????,????????????
  • ???????????????????????????,????Nu-????????,??????
    ???????????SN2???

33
??????????????,??1,4-????????????
34
(b)p????
  • (1) CC????????
  • CCp??CO p?????????,??-7-???????????????,??p??,??
    ??????????1011?,????????

35
(2) ????????
  • ??????????????,?????????????????????
  • (?)??????????(?)???????1014??

36
  • ?????(?)??????????(?)???5?,????(?)??????????(?)?3
    ??
  • ???????????????????????????,???????????

37
(3) ??????
  • ß?????????????
  • ?????????????-3-??-2-????????,??????????????????,?
    ???????????????????p???????????????,?????????(phen
    onium ion)???,??????????????????????,??????????,??
    ??????,????????????????????,???????

38
  • ??D?L????????????.

39
(c)s????
  • (I)????(IV)?350?

40
(6)???????
41
6. ???????
  • ???????????????????????????????,??????????????????
    ?????????
  • 1, 2????????????
  • ????????gt??gtH,?????????????????????

42
  • 1, 2-???????????????????????????P?????????????????
    ?
  • ?????????????????????????
  • ????????,?????????,?????????????????

43
  • ?????????????,????????????

44
???1, 2????????,??????????1, 3?????????
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