Question

Which, if any, of the following compounds can be prepared by an acetoacetic ester synthesis? Explain.

Short answer

Compound (a) and (c) cannot be prepared by acetoacetic ester synthesis. Only compound (b) can be prepared by acetoacetic ester synthesis.

Step-by-step solution

Determination of compound which can be prepared by acetoacetic ester

Compound (a) and (c) cannot be prepared by acetoacetic ester.

For synthesis of compound (a), 1,3-dibromobenzene is required. So the reaction will not proceed because aryl halides are not participating in S_N2 reaction.

For synthesis of compound (c), tert-butyl bromide is required. So the reaction will not proceed because tert-butyl halides are not participating in S_N2 reaction.

Hence, only compound (b) can be prepared by acetoacetic ester synthesis.

Preparation of compound (b)

The preparation of compound (b) is as follows,

The synthesis of compound (b)