Question

Draw a structure for each of the following:

a. ethyl acetoacetate

b. $\mathbf{\alpha }$-methylmalonic acid

c. a $\mathbf{\beta }$-keto ester

d. the enol tautomer of cyclopentanone

e. the carboxylic acid obtained from the malonic ester synthesis when the alkyl halide is propyl bromide

Short answer

a.

b.

c.

d.

e.

Step-by-step solution

Step-by-Step SolutionStep 1: Structure of ethyl acetoacetate (a)

Ethyl acetoacetate is used as a nucleophile in an alkylation reaction.The structure of ethyl acetoacetate is as follows;

Structure of (a)

α-methylmalonic acid (b)

The structure of $\mathrm{\alpha }$-methylmalonic acid is as follows;

Structure of (b)

β-keto ester (c)

A molecule having a ketone on the β-carbon of an ester. General β-keto ester structure. Ethyl acetoacetate is a typical β-keto ester. The structure of $\mathrm{\beta }$-keto ester is as follows;

Structure of (c)

The enol tautomer of cyclopentanone (d)

Keto-enol tautomer refers to a chemical equilibrium between keto form and enol form.

Structure of (d)

The carboxylic acid obtained from the malonic ester synthesis when the alkyl halide is propyl bromide (e)

The structure obtain from reaction of propyl bromide with the carboxylic acid of malonic ester is as follows;

Structure of (e)