18-18-3P d - 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

d) The preparation of Ethyl 2,2-dimethylpropyl ether using Williamson synthesis is as follows,

Preparation of ethers

One of the methods used for preparing ether is Williamson's ether synthesis. In this method, a nucleophilic displacement of the halide ion of an alkyl halide by an alkoxide ion occurs. Alkyl halide can be primary or secondary because it has the least steric hindrance.

The preparation of Ethyl 2,2-dimethylpropyl ether

d) According to Williamson ether synthesis, when an alkoxide (\({\left( {{\rm{C}}{{\rm{H}}_{\rm{3}}}} \right)_3}{\rm{CC}}{{\rm{H}}_2}{{\rm{O}}^{\rm{ - }}}\)) reacts with an alkyl halide (\({\rm{C}}{{\rm{H}}_3}{\rm{C}}{{\rm{H}}_2}{\rm{Br}}\)), an Ethyl 2,2-dimethylpropyl ether is formed along with a bromide ion.

             Preparation of Ethyl 2,2-dimethylpropyl ether