Chapter 18.7, Problem 14P

(a)

Interpretation Introduction

Interpretation: To prepare the given products from the reaction of a ketone with an alkyl halide.

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 removing a proton from an alpha carbon with a strong base, LDA, to form an enolate ion 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.

(b)

Interpretation Introduction

Interpretation: To prepare the given products from the reaction of a ketone with an alkyl halide.

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 removing a proton from an alpha carbon with a strong base, LDA, to form an enolate ion 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.