20.20Step 1:Nucleophilic addition of hydroxide ion to the carbonyl groupStep 2:Proton transfer to give neutral form of tetrahedral intermediateStep 3:Proton transfer from water to nitrogen of tetrahedral intermediateStep 4:Dissociation of N-protonated form of tetrahedral intermediateStep 5:Irreversible formation of formate ion20.21A synthetic scheme becomes apparent when we recognize that a primary amine may be obtained byHofmann rearrangement of the primary amide having one more carbon in its acyl group. This amidemay, in turn, be prepared from the corresponding carboxylic acid.CH3CH2CH2NH2CH3CH2CH2CO2HCH3CH2CH2CNH2OWaterHOHOHHydroxideionFormic acidOHCOHFormate ion
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