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Question 55 of 66

Q.The product formed by the reaction of an Aromatic aldehyde with primary amines is :

(a) Schiff's base
(b) Carboxylic acid
(c) Ketone
(d) Aromatic acid
Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2023MCQ· 1mImportance★★★★★
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Aromatic aldehydes react with primary amines by nucleophilic addition-elimination (condensation), losing a water molecule to form an imine (C=NC=N compound), historically named a Schiff's base.

The carbonyl carbon of the aromatic aldehyde (Ar−CHOAr-CHO) is attacked by the lone pair on the primary amine's nitrogen (R−NH2R-NH_2), giving a tetrahedral hemiaminal intermediate that then eliminates a water molecule to form a carbon-nitrogen double bond: Ar−CHO+H2N−R→Ar−CH=N−R+H2OAr-CHO + H_2N-R \rightarrow Ar-CH=N-R + H_2O. This class of imine products, especially those derived from aromatic aldehydes and amines, is traditionally named after Hugo Schiff as 'Schiff's bases,' and they are used as intermediates in synthesis and as chelating ligands. The product is neither a …

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