Aldehydes and Ketones
12.0 Addition of Nitrogen Nucleophiles
12.1 Mechanism and pH dependence of Rate of Reaction of Imine (>C = N-) Formation
12.2 Addition of Secondary Amines: Formation of Enamine
12.3 Mechanism for Enamine Formation
12.4 Addition of Ammonia: Reductive Amination
12.0 Addition of Nitrogen Nucleophiles
12.2 Addition of Secondary Amines: Formation of Enamine
12.3 Mechanism for Enamine Formation
12.4 Addition of Ammonia: Reductive Amination
Aldehydes and ketones react with primary amines and other ammonia derivative $(Z{\text{ }}-{\text{ }}N{H_2})$to form imines. An imine is a compound with a carbon – nitrogen double bond.
Compounds such as hydroxyl amine $\left( {N{H_2}OH} \right),$ hydrazine $\left( {N{H_2}N{H_2}} \right),$semi-carbazide $\left( {N{H_2}NHCON{H_2}} \right)$and primary amines $\left( {R{\text{ }}-{\text{ }}N{H_2}} \right)$are all derivatives of $N{H_3}$ because each has a substituent in place of one of the hydrogens of ammonia $\left( {H - N{H_2}} \right).$
The imine obtained from the reaction of a carbonyl compound and a primary amine is called a Schiff’s Base. The imine obtained from the reaction with $N{H_2}OH$ is called an oxime; the imine obtained from the reaction with hydrazine is called a hydrazone; and the imine obtained from the reaction of a semi-carbazide is called Semi-carbazone.
Phenyl substituted hydrazines react with aldehydes and ketones to form phenyl hydrazones.
