18-18-3P b - Organic Chemistry (Mcmurry)

Question

How would you prepare the following ethers using a Williamson synthesis?

1. Methyl propyl ether
2. Anisole (methyl phenyl ether)
3. Benzyl isopropyl ether
4. Ethyl 2,2-dimethylpropyl ether

Step-by-Step Solution

Answer

b) The preparation of anisole (methyl phenyl ether) using Williamson synthesis is as follows,

Synthesis of ethers

The ethers are synthesized by the best method known as Williamson synthesis, in which alkoxide and alkyl halide react together by a S_N2 reaction. By this method, symmetrical as well as unsymmetrical ethers obtain.

The preparation of Anisole

b) According to Williamson ether synthesis, an alkoxide (\({{\rm{C}}_6}{{\rm{H}}_5}{{\rm{O}}^{\rm{ - }}}\)) reacts with an alkyl halide (\({\rm{C}}{{\rm{H}}_{\rm{3}}}{\rm{Br}}\)) and forms Anisole as a product and a bromide ion. The reaction is as follows:

                         Preparation of Anisole