Question

Question: Draw two different routes to each of the following ethers using a Williamson ether synthesis. Indicate the preferred route (if there is one).

a.

b.

c.

Short answer

Answer

a.

b.

c.

Step-by-step solution

Step-by-Step SolutionStep 1: Williamson ether synthesis

This is one of the best methods to synthesize ethers that make use of the reaction between sodium or potassium alkoxide compounds with alkyl halides.

Synthetic routes for Williamson ether synthesis

To get the desired ether from the Williamson synthesis, two routes are possible. The route that involves less hindered alkyl halide (methyl halide / primary halides) is the most preferable one due to less steric hindrance.

This is an example of a bimolecular nucleophilic substitution reaction.

The possible routes for the given ethers

The two routes and the preferred route for the given ethers are as shown below.

a.

Representation of two different routes for a

b.

Representation of two different routes for b

c.

Representation of two different routes for c