(1)???????????

1
??????
????? ???
????????????----???
2
????????
1??????????????? 2??????????????????????? 3?????
4?????????? 5????? 6????????????? 7??????????
???????
3
??????
????????????? (?)???????? 1???????? (1)??????????
????????????? (2)??????????????????? (3)????????
????????,???????????,???????????????? 2???????
???????????????????????????????,??????????????????
?????
4
(?)???????? 1?????? (1)?????????????,?????1?1
0??????????????????????,??????????,?C11H24,?????
(2)??????????? A.????????????????????,????????
?????????? B.????????????,?1?2?3?4???????,??????
????? C.?????????,????????? D.????????????????
,?????????????????
5
2??????? ???????????????????????????????,???????
????????????????????????????????????
?????????,?????????????????????,????????,?????????
???
????????????????????????????????????????,?????
?????,???????????????????????????,?????????,??????
?????(?????)??????????,?????????????????,?????????
?????????????

6
??????????????????????????????????????????????
????????,???????,?????????????,????????????
???????,?????????????,??????
3???????????? ???????????????? (1)??????????????
??????????????,??,???????????13-2????????????????
,????????,??????? (2)???????????????????????,????
??????????? (3)??????????????????????????????????
? ?
7
??( CHO)???(OH)?,?????? CHO
????????????, CH2CH3? OH? CH3? Br
???,??????,?????????????????????????,???????????
????4 ?? 2 ?? 3 ?? 5 ????
?????? COOCH3 ,????????? OH?
NO2???,????????????????????,???????????????3
?? 2 ??????
8
???? (?)???????? ??????CnH2n2,?????????s
????,????????sp3?????????????,?????????????????(??
??)? (?)??????? ??????????,????????????,????????
???,?????????,????????,???????,???????????????????
????????,2????????,?????36.1??25??9?,?????
130?? 160?? 17??
9
(?)??????? ???????,???????,?????????????????????
??,??????????,????????? 1????? ??????????F2
gtCl2 gt Br2 gt I2,??????,???????????????????????????
?????????????,?????????? ??????????,???????????
?????,?????????????????????????????????? (1)????
??????250 400??,????????????????,??????????,????
??
Cl2 ? 2Cl
10
(2)????????????,?????????????????????????,???????
??????,????????????????????????Cl CH4 ?
HCl CH3 ???????????????,??????????????
CH3 Cl2 ? CH3Cl
Cl ????????????,???????? CH3Cl Cl
? CH2Cl HCl CH2Cl Cl2 ?
CH2Cl2 Cl (3)??????????,??????????,???????
???????????????????? Cl Cl ? Cl2
CH3 CH3 ? CH3CH3 CH3 Cl
? CH3Cl
2????? 3?????? 4????????????,??????
11
???? (?)???????? ??????????????????,???????????
?p???????,???????????? (?)?????
???????????????,??????????????,?????????,?????????
?,??????????? ???????,??????????????????p??????,
????,???????? ??????? 1????? (1)????
???????,?????????????????? (2)???
??????????????,????????,????????????
12
(3)???? ??????????????,???????,??????,??????? (4
)???(??) ?????????,??????????????????,????????????
??????????,????????? CH3CHCH2H2SO4?CH3CH(OSO3H)C
H3?CH3CH(OH)CH3H2SO4 (5)???? ????????,??ß
????????????,???????????????
CH2CH2HOCl?CH2(OH)CH2Cl 2????? (1)??????? ??????
?????????,??????????????????,??????
CH2CH2KMnO4H2O?CH2(OH)CH2(OH)MnO2KOH
13
??????????????,???????,????p???,s???????????,???
???????????,???????? CH2CH2 KMnO4 H2SO4 ?
2CO2 MnO2 CH3CHCH2 KMnO4 H2SO4 ?
CH3COOH CO2 CH3CHCHCH3 KMnO4 H2SO4 ?
2CH3COOH CH3C(CH3)CHCH3 KMnO4 H2SO4 ?
CH3COOH CH3COCH3 2???? ????,???????????????????
???????,?????????,??????????,????????????
????????????????(?????????????
???????),?????????? ?????????,????CH2
??????,RCH ?????,R2C ????????,??????????????????
?????
3????? 4?a H?????
14
(?)??????????? 1????????? ??????????????,?????Br
CH2CH2Br?,????BrCH2CH2Cl??,???ClCH2CH2Cl.
??????,?????????,?????????????,??????????,??????
?????????????Cl- ????BrCH2CH2Br???BrCH2CH2Cl??????
,????????????????,???????? ?????????,??p?????,??
??????????,?p????????????,???????????????????????
???????,????????????? ??????,??????????p??,?????
?????????????????p??????,??????????????????
??????????????????,???????
15
2?????????? ???????????????????????????????,????
???????????????????,???????????????????,??????????
????????????????????????????,?????,??????????,????
??????????????,????????????,?????,????????????????
??,?????,????????????????????? CH3 lt CH3CH2
lt (CH3)2CH lt (CH3)3C ????????,????????????????
?????????????,???????????????,???????????????,????
?????????,?????????????????????????,??????????,???
??????,??4?????????,????,?????

16
???? (?)???????? ??????CnH2n-2,????????,????????
???sp???????????????sp????,???2s?????2p????,?????
??sp????,sp????????sp2?sp3??????,??sp?????????????
?????sp??????,????????????????s?,????????????????,
????s?,??s??????????,???????????????????????????p?
?,?????????p?? (?)????? ????????????,???????????
,????????????,????????????????????????????????????
????????????????????????????????????????????,?????
??????
17
1????? (1)???? (2)??? ???????????,????????????
???????sp??????????sp2??????????,?????sp??????????
??,??????????????,????????????????????????????????
??,????????????????????????????????,??????????????
(3)???? ?????????,????????,????????,???????????
??????????????,?????????
?????????,???????????????,?????????????????,????
???????,?????????????? (4)??
???(10?H2SO4)?,????????????????,?10?H2SO4?5???????
,??????????,??????????????????????????????????????
(5)?? ??????,???????????,????????
18
2????? ?????????????,????? 3?????
??????????,????????????????????????????,??????????
???????,???????????????????,???????????????,??????
????????? 4??????? ?????????????????????sp??????
?????????,???????????????????????,??????,?????????
??????????????????????????,??????????????????????
????,????????????(???????)??,???????????,????????
??????????????????,???????????,??????????????????
????,???????????????????????????????,????????????
???????,????????????????????
19
??????? (?)?? 1,3??????,???????1???????????????
p??,?????s????,????????4?p??????????????4????????,
???p??????????????????????????,??????????,????????
???????????????????p??????????????p-p?????
?????????????????????????????,??s?????,????????,??
?????????????????????,??????,???????????????????p?
??????????????????,????????????
??????????1,3???????????????,????????,???????????
????????,?????????,??????
20
(?)?? 1???? ?????????????,??1,4-????1,3
??????????????,???????,1,3 ????????1,4
????????,?1,3 ???????1,4 ???????,1,3
???????? 2????? ?????,1,3 ?????????????????????
??????????,????????????,1,3 ????????????
????????????????,?????????????????????????,??1,2?
??????????????????????????,???C1?C4??????,????????
????,??C2?C3??,????????,??1,4???
21
?????????1,4?????,????????p?????????1,3???????
???,??????????,?????????,?????????????????????????
???,???????????????????????C1?C3,????C1??????????
??,??H ???C1? ?H ??C1?,?????????C2?p??????????
,??pp???????????C2???????,???????????????????????
???????,???????????? ????????????,??p?????,?C2?C
4????????? ??????,????????Br-
???????????,?C2?C4????????,??Br-
?????C2?,?????C4?,???1,2 ???1,4 ???
22
3????? ???????????????????????1,4-?????????????
???????,?????-???(Diels-Alder)???????????????,????
???????????,????????? ????????????????????,?????
????????????????,??????????????????????,?????????
23
????? (?)?????? ????????????????,?????????????????
?????????????????,???????????,??????????,?????????
??? (?)????????? ???????CnH2n,????????????????????
???????????????,??sp3??,??????????????s
???????????????,????????????,????????? (?)?????? 1
????? ???????????????????????????
24
2????? (1)???? ??????????,??????????????????????
??? (2)???? ??????????????????????,????????????
??,????????????????,????????????????????? ????????
?????,????????? (3)???? ??(?????)??????,????????
????????????????? ??? ???????,????????????? ?
???????????,??????? gt ??? gt ???? ???
???????????????? ????? ??????????????????????
???
25
????? (?)???? ??????,??????6??????sp2??,??????
???sp2????,????sp2???????1s????CHs?,???sp2???????
????sp2????????CCs??sp2???????,???120?,??????????
??????????????????p??,??????,??????????????p????p?
??????????,????????????,???????????????,??????????
,????????,????????????,??????????????? (?)????
?????????????????????,??????1,????????????????????
???????????????????????
26
(?)???? 1????? (1)?? ?????(FeCl3?AlCl3?FeBr3?)
?????? (2)???? ???????????????(????)?????,??????
??? (3)???? ??????????????????????,?????????? (4
)???? ???????? ??????????,???????,????????????
??1 ????????,???????????????,????????3ºCgt2ºC
gt1ºC,????????????????????????,?????????
27
???????? ??????????,???????????,?????????????
?? ????????,??????????????????????,?????????????
?????????????????????????????
???????????????,????????,???????,??????????,??????
?????? (5)?????????? ?????????????,?????????????
??? 2????? (1)?? ????????????????????????? (2)??
???????,????,??????????????????????
28
3????? (1)??????? ?????(??????????????????)???,???
?aH???????,???????,?????????? ??????aH,?????????
? ?????????????,??????????????,??????????,????????
?aH????????? (2)????? ????????,???????????,??????
???
O2
29
(?)??????????????? 1????? ?????????????????????
??,?????,???????????????????NHCH3 NH2 OH
OCH3 NHCOCH3 R X ? ??????????????????
?????,?????,?????????????,????N(CH3)3 NO2
CN SO3H CHO COOH ? 2???????? (1)???????
??????????,??????????,????????????,???????
???????????? ?????????????,????????????
30
(2)????????? ?????????????,????????????????????4
??2????
(?)???? 1?? ???????????????,?????????,????
????,?????????????????????? (1)????
?????a???????ß??,???????????a???????????,?????????
???
31
Cl2
H2SO4
32
3?????? 1931?,?????????????????????????????,??
???????????????????,???????????????????????p????
4n2?,?????????????????????,??4n2???
???1??????????X????????64,X??93.8,??6.2X????3??
??????????4???????????X???????CC,CC,CC
???,????CC?????CC??? (1)X?????
? (2)???X????????
????(1)????X? n (C) (6493.8)/12 5 n
(H) (646.2)/1 4 ?X?????C5H4 (2)X?????????
33
???2????????????????,????????
????

???3???????,?????????

????b , d????
34
???4???????????????????
????
???5???????????????
35
????
36
??????!