Question 17.4: How might you use an alkylation reaction to prepare ethyl 1-...

How might you use an alkylation reaction to prepare ethyl 1-methylcyclohexanecarboxylate?

S t r a t e g y

An alkylation reaction is used to introduce a methyl or primary alkyl group onto the α position of a ketone, ester, or nitrile by S_{N}2 reaction of an enolate ion with an alkyl halide. Thus, we need to look at the target molecule and identify any methyl or primary alkyl groups attached to an α carbon. In the present instance, the target has an α methyl group, which might be introduced by alkylation of an ester enolate ion with iodomethane.