Chapter 23, Problem 23.28P

Interpretation Introduction

(a)

Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized.

Concept introduction: The $\text{α}$ hydrogen attached to the $\text{β-}$ ketoester is acidic in nature and the hydrolysis and decarboxylation of the product obtained by substitution reaction of enolate ion with alkyl halide gives ketone.

Interpretation Introduction

(b)

Interpretation: The alkyl halide and ketone needed to prepare nabumetone are to be predicted.

Concept introduction: Carbonyl compounds on treatment with a strong base result in alkylation. The reaction is carried out in two steps: first is the removal of proton by base to generate enolate ion. The second step is the attack of nucleophillic enloate on the alkyl halide, displacing the halide and formation of alkylated product takes place via ${\text{S}}_{\text{N}}\text{2}$ mechanism.