How is benzamide converted into benzylamine reaction?
Answers
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The more reactive LiAlH4LiAlHX4 is required for the reduction of the amide to the corresponding amine (source). The carbonyl carbon of an amide is less electrophilic compared to a ketone, because electron density is donated by the amide nitrogen via resonance.
Bromine and hydroxide react with an carboxylic acid amide to yield an amine with one fewer carbon atom (Hofmann degradation). Br2BrX2 and KOHKOH react to form KOBrKOBr in situ, which transforms the amide into an intermediate isocyanate (R−N=C=OR−N=C=O). Hydrolysis of the isocyanate yields a carbamic acid R−NH−COOHR−NH−COOH, which decomposes to the amine R−NH2R−NHX2 and CO2COX2. As described in this paper, the reaction of PCl5PClX5 with carboxylic acid amides produces amidochlorides RCCl2NH2RCClX2NHX2 as intermediates, which break down to the corresponding nitrile RC≡NRC≡N and HClHCl.
Add Br2 and NaOH/KOH to benzamide and heat which will convert it to aniline or benzyl amine, this is called Hoffman Bromamide Degradation Reaction.