Chapter 20, Problem 20.29P

Interpretation Introduction

Interpretation:

Which products in problem $\text{20}\text{.28}$ will produce $\text{methyl cyclohexylmethanoate}$ when treated with ${\text{NaOCH}}_{\text{3}}$ is to be identified.

Concept introduction:

The reaction in which one form of an ester is converted to another form by changing the carbon skeleton of the (OR) part of the ester is called transesterification. The transesterification reaction is a nucleophilic addition-elimination reaction. In the first step, the nucleophile adds the electro-poor carbonyl carbon of an ester, which forces the bonding pair of carbonyl p bond onto the O atom. A negative charge is produced on that O, and a tetrahedral intermediate is formed. In the second step, the tetrahedral intermediate undergoes nucleophilic elimination to form the transesterification product. Transesterification is a reversible reaction.