Page 977 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

i. 961
SCH 3 PROBLEMS
N (C H ) N O
2 5 3
S + N
C H O CH 2 CH 3
2 5
2
j.
O
N O
CH 2 + N Ph N N
Ph
O O
k.

CN NC
CH3
CH 3
180°C

l.
CO CH
O C O HO 2 3
CH 3 2 O
H O
O 2 2 O
ArSe
m.
H
(C H ) N
N + 2 5 3 N
S S
CH Ph Ph
2
n.

CH 2 CH
(C H ) N 2
2 5 3
CH CCl
2
O
O
10.20. Both compounds 20-A and 20-B undergo solvolysis in polar solvents at low
temperature. The isolated product is 20-C. When 20-B is labeled with deuterium
it is found that there is complete scrambling of label equally among all positions
in the product.
H
H
D heat SO 2 D
Cl –60°C Cl
H H X
20-A 20-C 20-B
X = Cl, OH