
(a)
Interpretation:
Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.
Concept introduction:
Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an
To Find: To find the product formed when diethyl malonate undergoes bromination in acid catalyzed condition
(b)
Interpretation:
Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.
Concept introduction:
Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an
To propose : To propose the mechanism for the above reaction
(c)
Interpretation:
Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.
Concept introduction:
Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an
To Predict: Whether product will be more acidic than starting material or not

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Chapter 22 Solutions
Organic Chemistry, Binder Ready Version
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