Chapter 23.SE, Problem 64AP

Interpretation Introduction

Interpretation:

Given that reaction of pyrrolidine enamine of cyclohexanone with but-2-ene-3-one followed by hydrolysis and base treatment yields the product shown. Each step with its mechanism is to be given.

Concept introduction:

The steps involved in the reaction are i) Michael addition of enamine to cyclohexanone ii) A proton transfer iii) Hydrolysis to remove the amine iv) Abstraction of a proton from the diketone v) internal aldol reaction to form the second ring vi) Protonation and dehydration.

To give:

The mechanism of each step involved in reacting pyrrolidine enamine of cyclohexanone with but-2-ene-3-one followed by hydrolysis and base treatment to produce the product shown.