Question

Synthesis of methylcyclohexane from bromocyclohexane could be accomplished either by alkoxymercuration or by a Williamson ether synthesis. Describe both (short) syntheses. Which would you expect to be more successful, and why?

Answer 1

In the process of alkoxymercuration, a reaction between an alkene and a alcohol in the presence of mercuric acetate, produces an intermediate called alkoxymercury intermediate. This will react with sodium borohydride, a reducing agent, producing an eter.

In the Williamson Ether Synthesis, occurs a nucleophilic substitution reaction of an alkoxide nucleophile with an alkyl halide. As this is an easier way of producing ethers, it will be more successful than the Alkoxymercuration.