Chapter 21.5, Problem 6LTS

Interpretation Introduction

Interpretation:

To describe how the given compound can be prepared using acetoacetic ester synthesis

Concept introduction:

Acetoacetic ester synthesis is a process in which an halide is converted to a methyl ketone with two new carbon atoms (comes from acetoacetic ester).  By use of this method two new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

Please do remember that if alkyldihalide is used for acetoacetic ester synthesis a cyclic product is expected. (intramolecular acetoacetic ester synthesis)

Steps involved in acetoacetic ester synthesis are,

• Deprotonation of $\alpha$ carbon in acetoacetic ester
• Alkylation of enolate
• Hydrolysis of ester using aqueous acid
• Decarboxylation at high temperature