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Magazine Chapter 23: Q62. (page 924)
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?
Short Answer
Answer
(a)
(b)
Step by step solution
Generation of an enolate
The reaction of a carbonyl compound with a base generates an enolate (carbanion is generated at the alpha carbon).
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
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
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