H3C

CH3

CH3
CH3

H3C Br

Cl CH3

CH3

Br
Br
1 2Br2
H3C CH3 hν H3C
CH3
2 Cl
2 CH4 hν H3C Cl
Br CH3
Br
3 Li/Cu
H3C + H3C Cl H3C Br
CH3 CH3
CH3
4 Br2
H3C CH3 hν H3C Br
5 CH3
OH
NaOH
H C
H3C Br acetona 3
CH3
CH3
OH
6 Cl2
H3C OH
hν
CH3 Cl
CH3 CH3 H3C
OH
7 Li/Cu
OH + H3C Br H3C
CH3 CH3
Cl CH3
OH

8 H3C 2Cl2 H3C

OH
hν Cl
H3C CH3
CH3 CH3 H3C Cl

CH3
9 H3C Br2
CH3
hν H3C Br H3C
CH3
OH
CH3 CH3
10 Li/Cu
CH3
H3C
Cl + H3C OH
CH3 H3C Br
H3C Cl Cl

2Cl2 Cl
11 H3C
H3C CH3 hν
Cl H3C
CH3
H3C
12 CH3 CH3
CH3
Cl CH3 Li/Cu
H3C + CH3
H3C OH
H3C OH
CH3
Cl
Cl Cl
13 2Cl2
Cl
H3C CH3 H3C
hν H3C
Cl CH3
H3C
CH3 CH3
CH3
CH3
14 Cl
CH3
Li/Cu H3C OH
H3C + H3C OH

CH3
Cl CH3
Cl Cl
CH3
H3C
CH3
15 CH3 H3C
CH3 CH3

CH3
H3C OH NaBr CH3
+
Cl CH3 H
H3C Br

Cl CH3
CH3

CH3