Chapter 22, Problem 22.11P

Interpretation Introduction

(a)

Interpretation:

The curved arrow mechanism for the racemization process given in Eq 22.19 is to be shown.

Concept introduction:

Racemic mixture is the mixture of a compound which is optically inactive because half the molecules are the mirror image of other half. Racemization of a ketone involves enol as an intermediate. Enol form has carbon-carbon double bond which is planar and can be attacked from either above or below the plane. When solvent molecule attacks enol, then both the enantiomers are formed giving a racemic mixture.

Interpretation Introduction

(b)

Interpretation:

The curved arrow mechanism for the deuterium exchange given in Eq.22.18 is to be shown.

Concept Introduction:

The deuterium exchange reaction given involves keto-enol tautomerism. First the ketone gets converted into the enol form then again the enol takes deuterium from the solvent molecule and form the deuterated product.