46E - Organic Chemistry (Mcmurry)

Question

How would you prepare the following compounds using either an Acetoacetic ester synthesis or a malonic ester synthesis?

Step-by-Step Solution

Answer

The compounds (a) and (c) are prepared by malonic ester synthesis. The compounds (b) and (d) are prepared by acetoacetic ester synthesis.

Step 1: Preparation of compound (a)

The given compound is prepared by malonic ester synthesis. The preparation is as follows,

Step 2: Preparation of compound (b)

The given compound is prepared by acetoacetic ester synthesis. The preparation is as follows,

Step 3: Preparation of compound (c)

The given compound is prepared by malonic ester synthesis. The preparation is as follows,

Step 4: Preparation of compound (d)

The given compound is prepared by acetoacetic ester synthesis. The preparation is as follows,