?????? ????? ?????????

1
???????? ??????? ?

• ????? ?????????"? ???? ??? ???????? ????? ????
  ?? ????

2
???????????' 96

• ????? ????????? ??? ????? ?????? ?????? ????
  ?????? ?? ?????? ????????????? .
• ?????? ????????? ???????? ?????, ???? ??? ????
  ??? ????? ???? ??????.
• ?? ????? ?? ???? ?????? ?????.
• ????? ???? ????? ?????? ?? ??????? ???????
  ????? ?? ????? ????????? ??' 98-99

3
?????? ????? ????????? E2??' 100
????? ????
????
??????????
??? ????
??????????? ??????? ?????????? ??? ??????????
?????.
4
????? ?????????? ?????? ????????' 101
????? ?????????? ??????? ??????. ????? ??????
???? ??????????? ???? ?? ???? ?,????? ??????
??????. ????????? ?????? ???? ??????????? ????
?? ?????????? ????? ?. ???? ?????????? ????
?? ????? ????????? ??? ?????? ????????.
????? ?? ???? ? ???? ???? ?????
??????????.??? ??? ???? ????? ???? ???? ?????.
5
?????? ???????? ?? ?????? ????? ?????????? E2
??' 106-111
?. ???? ?????? ??? ????? ?????? ????? ????,
????? ????? ? ??? ????. ????? ????? ?? ????
? ??? ????. - ?? ???? ?? ??? ????
??????????? (????) ??? ?????? ??
????? ?? ???? ?, ???? ????? SN1. ?. ??????
?????? ????? ????? ???? ??? ???? ????? ???
?????? ?? ???? ? ??? ???.- ??? ??????.
6
?????? ???????? ?? ?????? ????? ?????????? E2
(????)
?. ?????? ??????? - ??????????? ???
???????????? ??? ???? ??? ????, ?????? ??????
????? ?????? ?? ???? ? ????? ????. -
NH2 ???? ???. ???? ?????? ???????
?????? ???? ???????????. ??? ????????????
???? ???? ?????? ????, ?????? ????? ????? ?
???? ????. - (CH3)3CO - ??????????
?????. ????? ??????????? ?????? ????.
??? ?????? ???? ? ?? ???? ?????? ????.
?????????? ??? ????? ????? ?????? ???? ?????
?? ????? ?? ???? ?. - F - ??? ?????
????? ?????? ????.
7
?????? ???????? ?? ?????? ????? ?????????? E2
(????)
?. ???? ????? CH3CH2CH2Br OH(aq) ?
CH3CH2CH2OH Br(aq) ????????? CH3CH2CH2Br
OH(C2H5OH) ? CH3CHCH2 Br(C2H5OH) ???
?????? ?? ????? ???????. ???OH(aq) ???
?????????? ??? ???? ????OH(C2H5OH) ????
??????? ??? ??????????? ???? ???? ?? ?????? ???
??????????? ????. ??? ?????? ???? ????? ??
???? ??????????? ???? ?? ???? ?????
?????????? ?? ?????.
8
?????? ???????? ?? ?????? ????? ?????????? E2
(????)

• ?. ?????????
• ??????? ?????? ?? ????? ??????????
  ????? ???? ???? ????? ??????.
• ????' ????? ???? ???? ????????? ?????
  ?????? ????? ???????? ?????? ???? ????.
  ???? ????????? ?????? ????????? ??? ?????
  ???? ????? ????????? ????? ????? ??? ?????'
  ????.

9
??????? ??????? ??? ??????? ???? ?????????? ?????
??' 111-112
10
????????? ???? ??????????

• ?????????? ?????? ????? ????? ???? ??????, ??
  ???? ?????? ??????? ???? ????.
• ???? ????? ?? ?????????, ?????? ????? ?????
  ?????????? "???????" ?????? ?????????, ?? ????
  ???? ?????? ????? ????? ?????????? "???????"
  ?????? ?????. ??? ????? ????? ????' ?? ?????
  ?????????? ????? ????.

11
E1 ????????? ??????? ?????' 117
??? ?????? ??? ????????
????? ??????????
12
E1 ????????? ???? ?????

• ?????? ???? ??? ????
• ?????? ???? ???????.?????????? ???.????
  ?????.????????? ?????.

13
????????? ???? ??????? ???? ???????
????? SN2 E2
???? ?????? ?? ????? ?????? ??????gt??????????? ??? ????? ?? ????? ??????? gt ??????????? ??? ????? ?????
??????????? ?????? ???? ????? ??? ??? ????? ??????, ????? ???? ???? ???? ????? ??? ???? ???????? ??????, ????? ???? ????
???????? ????? ?????
??? ?????? ??????
14
?????- ????? ??? ?????????
??? ?????? ??? ?????? ??? ?????? ??? ??????
????? ???? SN1 SN2 E1 E2
?????? ?? ????? ????? ???????? ?? ????? ????? ???????? ????? ??? , ??????? ?????
?????? ???? ?? ????? ????? ???? ???? ??? ?? ????? ???? ??? ?????? ???' ????? ???? ?? ????? ????? ???????? ?????? ????????? ?????
??????? ????? ???? ???? ??? ??? ????? ??? ????? ?? ????? ????? ???????? ?????? ???????? ????? ????? ???????? ?????? ????????? ?????
15
?????? ?????? ????????????????? CH3Br Nu ?
CH3Nu Br
?????????? ?????? ????? ?????????? ?????? ?????
H2OCH3OH 1 CH3O 25,000
NH3 700 I 100,000
Cl 1000 CN 125,000
OH 16,000 HS 125,000
16
???? ???? ?? ?????? ??????? ???????HX(aq)
H2O(l) ? H3O(aq) X(aq)
???? ??? ???? ????? pKa-log Ka ????? ????? ????
CH3CH2O 16.00 CH3CH2OH
OH 15.74 H2O
CN 9.31 HCN
CH3COO 4.76 CH3COOH
F 3.45 HF
NO3 -1.3 HNO3
???? ??? Cl -7.0 HCl ????? ????
17
?????? ?????? ?????? ???????????? RL Nu ?
RNu L
????? ????? ?????? ????? ?????? ?????
NH2- -0 ???? ????
CH3O- -0
OH- -0
F- 1
Cl- 200
Br- 10,000
I- 30,000 ???? ????
18
?????? ?????? ?????? ???????????? HL H2O ?
H3O L
????? ????? pKa ?????
???? I -10 HI
Br -9 HBr
Cl -7 HCl
RSO2O -6.5 RSO2OH
H2O -1.7 H3O
F 3.2 HF
HS 7.0 H2S
CN 9.2 HCN
OH 15.7 H2O
????? RO 16-18 ROH
19
???? ??? ??????? SN2 ????? ??????Br-
CH3CH2CH2CH2Br N3- ? CH3CH2CH2CH2N3
K(solvvent)K(metanol) ???
1 CH3OH ????? ?????
7 H2O ????? ?????
1300 (CH3)2SO ????? ??????
2800 (CH3)2NCHO ????? ??????
5000 CH3CN ????? ??????
20
???? ??? ??????? SN1 ????? ??????HCl (CH3)3CCl
ROH ? (CH3)3COR
K(solvvent)K(etanol) ??????? ???
1 C2H5OH
100 40 H2O60 C2H5OH
14,000 80 H2O20 C2H5OH
100,000 H2O
21
?????? ????????? ??????? ?????'120
H2SO4

H2O
22
?????? ????? ????????' 123

• ??? ?
• ??? ?'

23
???? ?????? ??????

• ??? ?'

24
????? ????? ???????'127
25
????? ???? ??????' 128

• C2H4(g) Br2(l) ? C2H4Br2(g)

???? ???????? ???(kJ/mol)
C-C 346
CC 610
26
??? s ??? p
27
??? p ??????????' 129

• ????? ??????? ???? ?????????? ?????? ?? ??? p
  ????? ??? ?????? ???? ?????? ?? ??? ???? ????
  (????? ???? s).
• ???????? ??? p " ??????" ???? ???? ?????? ????
  ?????? ???????????.
• ????????? ????? ?????? ???? ??? ??????
  ????????? ????? ???????? ????? ???? ?????????

28
?????? ????? ????????????' 131
CH3CHCHCH3 HBr ? CH3CH2CHBrCH3
??? ?' ????? ???????????
??? ?' ????? ????? ????
29
????? ???? ????????? ?????? ??' 133
??? ???????? ??????
?????? ?????
30
??? ????????????' 134

• ?????? ????? ???????, ???? ??? ????? ????? ??????
  ?? ??????? HX ???? ???????? ????? ?? ?????? ???
  ???????? ????? ?????.
• ??? ????????? ?????? ??????? ???? ???? ???? ????
  ???? ???? ????? ???????????.
• ???? ?????? ???? ????? ??? ????? ????? ??????
  ????? ???? ?? ???? ??????, ???? ??? ????????.
  ???? ???? ???? ?? ????? ?????? ????? ??? ?????
  ????? ??????.

31
??? ??????????
32
????? ??? ???????????? ????? ????? ????? ??' 138