Q44E - Organic Chemistry (Mcmurry)

Question

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

Step-by-Step Solution

Answer

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

Step 1: 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.

Step 2: Preparation of compound (b)

The preparation of compound (b) is as follows,

The synthesis of compound (b)