Alkyl halide Aryl halide R X Ar X

1
Alkyl halide

• Alkyl halide ???? Aryl halide ????????????
  ??? R - X ???? Ar - X
• ????????????????????? ? ????
  ???????????????? ?????????? ?????? ????
• ???????????????????

2
????????? Alkyl halide

• Primary alkyl halide ??????????????????????
  ???????? 10 ????????????
• Secondary alkyl halide ?????????????????????????
  ????? 20 ????????????
• Tertiary alkyl halide ??????????????????????????
  ???? 30 ????????????

3
????????? Alkyl halide
4
Dihalide

• Geminal dihalide or gem-dihalide
  ??????????????????? 2 ???????????????????????????
  ?????????

Vicinal dihalide or vic-dihalide
??????????????????? 2 ????????????????????????????
?????????????
5
Alkyl halide

• ???????????? ??? IUPAC

• ???????????? halogen ???????????????????????????
  ?? ????????????????????????? ????

2-bromo-3-chloro-1-pentanol
2-chloro butane
6
Alkyl halide

• ???????????? ??? common name
• ???????????????? alkyl ??????????????????
  halide ????
  

ethyl bromide
sec-butyl bromide
isobutyl bromide
7
Alkyl halide

• ???????????? ??? common name (???)
• ????? halogen ??????? 1 ????? ???????????????
  ????

methylene chloride
carbon tetrachloride
chloroform
8
?. 2-bromo-5-chloro-3-hexene ?.
4-bromo-5,6,7-trichloro-3-octene?.
1-bromo-3-chlorocyclohexene ?. Iodoform?.
allyl bromide ?. vinyl chloride
??????????????????????????????????????????????????
??
9
??????????????????????????????????? IUPAC
2,3-dibromo-4,5-dimethylheptane
10
??????????????????????????????????? IUPAC
2,3-dichloro-5-methyl-2-hexene
11
??????????????????????????????????? IUPAC
2-chloro-3,3-dimethyl-1-phenylbutane
12
?????????????????????????????????

• 1. Free-radical halogenation of alkanes

???
???
13
?????????????????????????????????

• 2. Addition to alkenes and alkynes

????? EA ??? Cl2, Br2, I2, HCl, HBr ???? HI
14
?????????????????????????????????
3. Electrophilic aromatic substitution
15
?????????????????????????????????
4. Reaction of alcohols with hydrogen
halides
16
Mechanism ?????? 10 alcohol
17
Mechanism ?????? 20 ??? 30 alcohol
18
?????????????????????????????????
5. Reaction of alcohols with thionyl chloride
19
?????????????????????????????????
6. Reaction of alcohols with phosphorus
trihalide
20
???????????????

• ??????????? ??????????????????????????????????????
  ?????

?????????????????????????????????????????????
????????????????????????????
21
????????????????????????????

• 1. ??????????????????????????????????

22
????????????????????????????

• 1. ?????????????????????????????????? (???)

23
????????????????????????????
1. ?????????????????????????????????? (???)
24
????????????????????????????
1. ?????????????????????????????????? (???)
25
Mechanism ?????????????????????
????????????????????? SN1
26
Mechanism ?????????????????????
????????????????????? SN2
27
????????????????????????????

• 2. ???????????????????

???????????????????????????? Saytzeff
28
Mechanism ??????????????????????
?????????????????????? E1
29
Mechanism ??????????????????????
?????????????????????? E2
30
??????????????????????????????????????????????????
???????
31
????????????????????????????

• 3. Preparation of Grignard reagent

Grignard reagent ?????????????????????????????????
???????
32
????????????????????????????

• 4. Reduction of metal and acid

33
????????????????????????????

• 5. Coupling of alkyl halide with
  organometallic compound

34
????????????????????????????
????????????