Question

Give two syntheses for (CH3)2CH-OCH3, and explain which synthesis is better.

Short answer

Two methods for syntheses of (CH₃)₂CH-OCH₃,

1. Williamson synthesis

2. Alkoxymercuration-Demercuration

Step-by-step solution

Alkoxymercuration-Demercuration reaction

It is stereospecific reaction results in formation of ether via Markovnikovs addition. In this reaction alkene is reacted with Hg²⁺ salt an oxygen nucleophile (alcohol) to from organomercury intermediate. This intermediate carbon mercury bond is then converted to carbon-hydrogen by using NaBH₄.

Advantage of Alkoxymercuration-Demercuration

Alkoxymercuration-Demercuration is a better method for the synthesis of ether as we can synthesize any type of ether with this method. But with Williamson synthesis, the alkyl halide used must be primary so it is not possible to synthesize branched ether with this method.