Q62. - Organic Chemistry

Question

Question:

(a) Draw two different haloketones that can form A by an intramolecular alkylation reaction.

(b) How can A be synthesized by an acetoacetic ester synthesis?

Step-by-Step Solution

Answer

Answer

(a) 

(b)

Step 1: Generation of an enolate

The reaction of a carbonyl compound with a base generates an enolate (carbanion is generated at the alpha carbon).

Step 2: Haloketones involved in the synthesis of A

The compound A can be synthesized using the given haloketones.

The reaction of the haloketones in the presence of a base yielding compound A is shown below.

                            Haloketones used in the synthesis of A

Step 3: Synthesis of A by acetoacetic ester synthesis

The reaction of the given substituted acetoacetic ester with base generates an enolate.

The enolate attacks the electron-deficient carbon atom (the carbon atom attached to the electronegative bromine atom).

The basic hydrolysis of the obtained product yields compound A.

Synthesis of A by acetoacetic ester synthesis