In the conversion of (C) to (E), (E) is Bu−NH2. This reaction is called:
A
haloform reaction
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B
hofmann reaction
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C
hofmann bromamide reaction
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D
hofmann bromamide rearrangement reaction
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Solution
The correct option is D hofmann bromamide rearrangement reaction The reaction is Hofmann bromamide rearrangement reaction. It is also called Hofmann degradation or Hoffmann bromamide reaction. The cyanide ion attacks compound A to from a nitrile which on partial hydrolysis forms amide (compound C). Compound C reacts with NaOBr to from butyl amine (compound E) CH3CH2CH2CH2ClCN−−−−→−Cl−CH3CH2CH2CH2CNpartial hydrolysis−−−−−−−−−−→
CH3CH2CH2CH2CONH2NaOBr−−−−→CH3CH2CH2CH2NH2 In this reaction, the product amine contains one C atom less than the substrate amide.