Vo Lam Hoai Trung

BTCEIU19009

ORGANIC CHEMISTRY 2
Homework 2
13.34
1) NaNH2 1) NaNH2 Na, NH3(l) CH3CO3H O

2) CH3Br 2) CH3Br
Lin
dla H2 ,
r' s
ca
tal
ys O
t CH3CO3H

13.37
a.

1) CH3CO3H
2)MeMgBr OH
3)H2O
C
H3

r
C

gB
O3

H M
H

2) Me
2O
1)

O
(Racemic)

b.
1) Hg(OAc)2, MeOH

2) NaBH4 OMe

(Racemic)
c.
MeS
1) CH3CO3H
2)NaSMe OH
3)H2O
(Racemic)
3
3

2
O
(Racemic)

d.
OH 1) Na OEt

2) EtCl

e.
OH 1) Na O

2) O OH

3) H2O

O
Na

2O
1)

2) H

ONa

f.
OH
Cl 1) Mg, diethyl ether

2) O

3) H2O
 13.38
a.

O HO
O H H
O

CH2CH3

b.

H Et I
O H O O Et

c.

O
O H H HO
O

C C H

d.
H H
H O OH
O H O

SMe MeS

13.40
We have the structure of cis-1,4-dibromocyclohexane: (C6H10Br2)

Br Br

Since the structure of the compound B and product have the same number of C and H, we can
expect that the bond that are cleavage through the reaction is 2 C-O bonds to replace by 2C-Br
bonds in products and retain the cyclohexane ring. And with the treating reagent is HBr, we can
expect the compound B have structure of ether (which have no π bonds presents) with the C -O –
C bonds at 1,4 location in the cyclohexane ring. So the structure of compound B is:
O Con.c HBr
O Br Br
13.42
In both case a) and b) we will have the Alkoxymercuration – Demercuration reaction in which
the nucleophile (MeO- and PhO-) will attack in the more substituted position in πbond.
a.
1) Hg(OAc)2, MeOH
OMe
2) NaBH4

b.
OH

1) Hg(OAc)2 O

2) NaBH4