Question

1. Draw the major products only expected from the reaction of 2-bromo-3-methylpentane with each of the following:

A. CH3CH2O-

B. (CH3)3CO-

C. CH3CH2OH

2. Starting with an appropriate alkyl halide and using any other needed reagents, how could you synthesize the following?

A. butyl sec-butyl ether

B. CH3COCH2CH3
||
O

C. (CH3)3CCH=CH2

Answer 1

1. The major products formed in each case are shown below.

(A) Elimination reaction to form the more substituted zaitsev product.

(B) Elimination reaction with a hindered base gives the Hofmann product which is the least substituted alkene.

(C) Ether formation by reaction of alkyl halide with alcohol.

2. Synthesis of various compounds shown below.

(A) Synthesized by Williamson's reaction strategy.

(B) Synthesized by grignard reangent formation and couplign with an aldehyde followed by oxidation of it to ketone.

(C) Synthesized by Williamson's reaction strategy.

The major products formed and the synthetic schemes are shown below.