18-18-3P c - 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

c) The preparation of benzyl isopropyl ether using Williamson synthesis is as follows,

Method for the preparation of ethers

The best method to prepare simple or mixed ethers is the Williamson ether synthesis method. The best alkyl halides used are methyl and primary alkyl halides because they have least steric hindrance. 

The preparation of benzyl isopropyl ether

c) According to Williamson ether synthesis, when an alkoxide (\({\left( {{\rm{C}}{{\rm{H}}_{\rm{3}}}} \right)_2}{\rm{CH}}{{\rm{O}}^{\rm{ - }}}\)) reacts with an alkyl halide (\({{\rm{C}}_{\rm{6}}}{{\rm{H}}_{\rm{5}}}{\rm{C}}{{\rm{H}}_2}{\rm{Br}}\)), a Benzyl isopropyl ether is formed along with a bromide ion.

                      Preparation of Benzyl isopropyl ether