Page 1081 - Advanced Organic Chemistry Part B - Reactions & Synthesis

11.2. Suggest a short series of reactions that would be expected to transform the 1057
material on the right into the desired product shown on the left.
PROBLEMS
(a) CH 3 CH 3

CH 3 CH 3
F

(b) H

H

(c) Cl
O
CH 3 CCH 2 CH CO H CH 3
2
2
Cl
H
(d) OC 6 5
N NO
O 2 2
(e)
Cl
CO 2 H
Cl
NH 2

11.3. Write mechanisms that would account for the following reactions:
(a) OCH 3 OCH 3 OCH
HNO 3 NO 2 3
+
Ac O
2
Br Br NO 2

(b) OCH 3 OCH 3
O
NH (I)
3
CCH –
+ CH 3 2
CH CCH
Br 2 3
O
H CH 3 H H CH 3
(c) CO 2 – H H + H C
+ CH 3 2 CH H
N 2 + CH 3 H H Ph
H CH 3 ~6%
~74%
(d) OCH 3 OCH 3
BF 3
CC H
2 5
CH O O CC H CH O OH O
3
3
2
2 5