(1)

H2C

CHCH

H
H3C C C CH2
H
I

+ HI

CH2

H3C C CH CH2

(2) Name (IUPAC):

(H3C)2HC

1,2

1,4

CH2CH(Br)CH3

6-bromo-2-methyl-3-heptyne
(3)

H3C

CH2CH3

H3C

CH2CH3

Br

+ HBr

(Mark??)
H3C

Br

CH2CH3

(Now Mark.....)

H3C

(4)

Br

Br

CH2CH3

H3C

Br

Br

CH2CH3

(CH2)3CH3
Cl

(Anti)

+ 1 mol Cl2

(CH2)3CH3

Cl

(Anti-Mark) + 1 mol HBr, peroxides

(Mark)

+ 1 mol HBr

C
H

+ 2 moles HBr

C
H

(CH2)3CH3

Br

Br

Br

Br

Br

(CH2)3CH3

(CH2)3CH3

(Mark)
H

(CH2)3CH3

(2) 1 mol HBr

(1) H2, Lindlar

(Mark)

+ 2 moles Br2/CCl4

(Syn)

Br

Br

Br

H
C

H
C

Br
(CH2)3CH3

(CH2)3CH3