Page 1080 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1056 Problems

CHAPTER 11 (References for these problems will be found on page 1289.)
Aromatic Substitution
Reactions

11.1. Give reagents and reaction conditions that would accomplish each of the
following transformations. Multistep schemes are not necessary. Be sure to
choose conditions that would lead to the desired isomer as the major product.
(a)
CH 3 Br CH 3 C N

(b) CO 2 CH 3 CO CH 3
2
I

(c) CH OC CH CHCO C H CH O
3
3
2 2 5
2
C H
CO 2 2 5
C
CH O O CO C H CH O
3
3
2 2 5
O CH O CO C H
2 2 5
CH 3 3
(d)
CH(CH ) CH(CH )
3 2
3 2
I
(e)
HC CHCH CH
NH 2 2
NO 2 NO 2
(f) O CCH 3 O CCH 3
2
2
O O
CH C O 2 CCH 3
3
O 2 CCH 3
O
(g)
CH O NH 2 CH O F
3
3
CH O CH O
3
3
(h)
3
2
CH O C CH O C
2
3
NH 2 OCH 3
O
(i)
CH CO 2 HO
3
CH 3
CH 3 O CCH 3 CH 3 OH
2