Chapter 12, Problem 54P

Interpretation Introduction

Interpretation:

An explanation for the formation of the same anion being formed by the loss of the most acidic proton from both $\text{1-methyl-1,3-cyclopentadiene}$ and $\text{5-methyl-1,3-cyclopentadiene}$ is to be provided.

Concept introduction:

The most acidic proton in cyclopentadiene and its derivatives (except $\text{C5}$ disubstituted) is the one bonded to $\text{C5}$.

A tertiary carbanion is unstable because of the three inductive electron donating groups bonded to the negatively charged carbon.