Chapter 22.SE, Problem 27MP

Interpretation Introduction

Interpretation:

A mechanism for the reversible equilibrium isomerization of 2-substituted-2-cyclopentanones to 5-substituted-2-cyclopentanones is to be proposed.

Concept introduction:

The steps involved in the reversible equilibrium isomerization of 2-substituted-2-cyclopentanones to 5-substituted-2-cyclopentanones are i) abstraction of a proton from the γ-carbon to form a resonance stabilized enolate ion ii) Protonation at the α- carbon iii) Abstraction of a proton from other α- carbon to form a different resonance stabilized enolate ion iv) Protonation of the γ- carbon.

To propose

A mechanism for the reversible equilibrium isomerization of 2-substituted-2-cyclopentanones to 5-substituted-2-cyclopentanones.