Page 1020 - Advanced Organic Chemistry Part B - Reactions & Synthesis

996 O
Br –
CHAPTER 10 CH O
3
Reactions Involving
Carbocations, Carbenes, (CH )
and Radicals as Reactive 10-7 2 n
Intermediates
a – c; n = 1– 3
10.8. Predict the major product of the following reactions:
(a) O (b) O
CuSO 4
–
OSO 2 Ar 1) OH, 110°C
CCHN 2
toluene, 105°C,
2 h 2) H +
H
(c) CH 3 (d) CH 3
H H O
Cu(acac) 2
CH 3
t - AmO – (CH 2 ) 2 CCCH 3 benzene, 80°C,
H
CH 3 12 h
N 2
CH 3 O OH
OTs
(e) O CHCH 2 CH 2 (f) O
CH 3
O
SnCl 4
S KOH
benzene,
CH 3
10°C, H 2 O, 100°C,
CH 3
Cl
(g) CH 3
H
CH 3 1) CH 3 SO 2 Cl,
OH
CH 3 O CH 3 (C 2 H 5 ) 3 N
H + –
CH 3 2) K O - t - C 4 H 9
CH 3
OH
10.9. Short reaction series can effect formation of the desired material on the left
from the starting material on the right. Devise an appropriate reaction sequence.
(a) OSi(CH 3 ) 3 O (b)
OH
CH 2 OH
(c) OCH3 HOCH 2 OCH 3 (d) CH 3 CH 3
H H
H 2 C CH CH 3 CH 3 CH 3
O O OH
CH 3 CO 2
O CHCH 2 H CH 3 CH 3
H
CO 2 CH 3 CO 2 CH 3
(e) CH 3 (f) H H
CH 3 H H
H
O
CH 2 OH O
H H O
CO 2 CH 3
CH 3 H
CH 3 H H
O
(g) CH 2 OCH 3 (h)
O OH O
O
O
H OCH 2 Ph H OCH 2 Ph O
Ph O Ph O
O