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Wolff rearrangement When alpha-Diazok...

Wolff rearrangement
When `alpha`-Diazoketones are photo-irradiated or heated at high temperature or reacted with silver oxide or silver salts at room temperature, they loose nitrogen and rearrange to form ketene.
The ketenes reacts rapidly with water, alcohol and amines. Therefore, the reactions called Wolff-rearrangement.

, Product (A) is :

A

B

C

D

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The correct Answer is:
B
Intramolecular rearrangement
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Amines are less reactive in substitution reactions. Their reactivity is much lesser than alcohols and alkylflourides towards substitution. Protonation of the amino group makes it a better leaving group, but not nearly as good a leaving group as a protonated alcohol. Protonated amino groups cannot be displaced by OH^(-) because it would react immediately with the acidic hydrogen which would convert it in to a poor nucleophile. The leaving group in quartenary ammonium ion has about the same leaving tendency as a protonated amino group but does not have acidic hydrogen. The reaction of a quartenary ammonium ion with hydroxide ion is known as Hoffmann elimination reaction. The leaving group is tertiary amine. Since a tertiary amine is only a moderately good leaving group, the reaction requires heat. The carbon to which the tertiary amine is attached is designated as alpha carbon. When the hydroxide ion starts to remove a beta H from a quartenary ammonium ion, the leaving group does not immediately start to leave because a tertiary amine is not a good leaving group. As a result, a partial negative charge builds up on the carbon from which the proton is removed. The compounds 'C' in question number 31 on heating with moist silver oxide gives

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