Chapter 22.7, Problem 14P

Interpretation Introduction

Interpretation:

Among phenylacetone, acetophenone and 3,3-dimethyl-2-butanone which cannot be prepared by acetoacetic ester synthesis is to be stated.

Concept introduction:

Acetoacetic ester synthesis converts an alkyl halide in to a methyl ketone having three more carbons. The methyl ketone part comes from acetoacetic eater while the remaining carbon comes from the primary alkyl halide. The reaction occurs in three steps 1) enolate ion formation ii) ^SN² attack of the enolate anion on the alkyl halide iii) hydrolysis and decarboxylation.

To state:

Among phenylacetone, acetophenone and 3,3-dimethyl-2-butanone which cannot be prepared by acetoacetic ester synthesis.