18-18-3P a - 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

a) The preparation of methyl propyl ether using Williamson synthesis is as follows,

Williamson synthesis

In Williamson synthesis,  S_N2reaction occurs between alkoxide and alkyl halide and an ether product is formed. It is the best method used for the synthesis of simple as well as mixed ethers.

The preparation of methyl propyl ether

a) According to Williamson ether synthesis when an alkoxide ( ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{O}}^{-}$or ${\mathrm{CH}}_3{\mathrm{O}}^{-}$) reacts with an alkyl halide ( ${\mathrm{CH}}_3\mathrm{Br}$or ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{Br}$ ), it forms Methyl propyl ether and a bromide ion.

              Preparation of Methyl propyl ether