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Question
Identify 'A' and 'B' in the following reaction and rewrite the complete reaction.
CH3−CH2−Br+AgCNΔ→ANaC2H5OH→B.
Explain Hoffmann bromamide degradation reaction.
CH3−CH2−Br+AgCNΔ→ANaC2H5OH→B.
Explain Hoffmann bromamide degradation reaction.
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Solution
CH3−CH2−Br+AgCNΔ−−−−→−AgBrCH3−CH2−NC A, ethyl isocyanideNaC2H5OH→CH3−CH2−NH2−CH3B, ethyl methyl amine Ethyl bromide reacts with silver cyanide to form ethyl isocyanide.Na/ethanol reduces ethyl isocyanide to ethyl methyl amine.
Hoffmann bromamide degradation reaction:
Treatment of amide with bromine and aqueous ( or alcoholic) NaOH, a primary amine is obtained.
CH3−CONH2+Br2+4NaOH→CH3−NH2+Na2CO3+2NaBr+2H2O
The product amine has one C atom less than starting material amide.
Ethyl bromide reacts with silver cyanide to form ethyl isocyanide.
Na/ethanol reduces ethyl isocyanide to ethyl methyl amine.Hoffmann bromamide degradation reaction:
Treatment of amide with bromine and aqueous ( or alcoholic) NaOH, a primary amine is obtained.
CH3−CONH2+Br2+4NaOH→CH3−NH2+Na2CO3+2NaBr+2H2O
The product amine has one C atom less than starting material amide.
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