Chapter 17.8, Problem 17P

(a)

Interpretation Introduction

Interpretation: The following given compounds prepared from cyclohexanone using an enamine intermediate.

$\text{2-propylcyclohexanone}$

Concept introduction: To increase the carbon chain, substituting an alkyl group on alpha carbon of a carbonyl group is called alkylation.

Alkylation is carried out by reaction of a ketone with a secondary amine in the presence of an acid to form an enamine and then adding an appropriate alkyl halide.  The alkylation is a ${\text{S}}_{\text{N}}\text{2}$ reaction.  The alkylation works best with a primary alkyl halide.

Acylation is carried out by reaction of a ketone with a secondary amine in the presence of an acid to form an enamine and then adding an appropriate acyl halide.  The acylation is an addition reaction.

(b)

Interpretation Introduction

Interpretation: The given compounds prepared from cyclohexanone using an enamine intermediate.

$\text{2-propanoncyclohex-1-one}$

Concept introduction: To increase the carbon chain, substituting an alkyl group on alpha carbon of a carbonyl group is called alkylation.

Alkylation is carried out by reaction of a ketone with a secondary amine in the presence of an acid to form an enamine and then adding an appropriate alkyl halide.  The alkylation is a ${\text{S}}_{\text{N}}\text{2}$ reaction.  The alkylation works best with a primary alkyl halide.

Acylation is carried out by reaction of a ketone with a secondary amine in the presence of an acid to form an enamine and then adding an appropriate acyl halide.  The acylation is an addition reaction.