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Q8.1(x):
What is meant by the following term? Give an example of the reaction. (x) Schiff’s base

Solution :

Theoretical Definition of Schiff’s Base

A Schiff’s base is a chemical compound containing a carbon-nitrogen double bond, where the nitrogen atom is connected to an aryl or alkyl group but not to a hydrogen atom. They are systematically classified as imines. They are synthesized via the nucleophilic addition of a primary amine ($R-NH_2$) to an aldehyde ($R'-CHO$) or a ketone ($R'_2C=O$), followed by the elimination of a water molecule [Per the mechanism of nucleophilic addition-elimination].

General Reaction Mechanism

The formation follows the general stoichiometry:

$R-CHO + R'-NH_2 \rightleftharpoons R-CH=N-R' + H_2O$

The reaction proceeds through the following steps:

  • Nucleophilic Attack: The lone pair on the nitrogen of the primary amine attacks the electrophilic carbonyl carbon of the aldehyde/ketone, forming a hemiaminal intermediate ($R-CH(OH)-NH-R'$).
  • Proton Transfer: An internal or external proton transfer occurs, converting the hydroxyl group ($-OH$) into a better leaving group ($-OH_2^+$).
  • Dehydration: The elimination of $H_2O$ leads to the formation of the $C=N$ double bond.

Illustrative Example: Formation of N-Benzylideneaniline

The reaction between Benzaldehyde ($C_6H_5CHO$) and Aniline ($C_6H_5NH_2$) results in the formation of N-benzylideneaniline, a classic Schiff’s base.

$C_6H_5CHO + C_6H_5NH_2 \xrightarrow{H^+} C_6H_5CH=N-C_6H_5 + H_2O$

Structural Representation

C₆H₅-CH=O + H₂N-C₆H₅ C₆H₅-CH=N-C₆H₅ + H₂O Aldehyde Primary Amine Schiff's Base

Summary Comparison Table

Component Chemical Formula
Carbonyl precursor $R-CHO$ or $R_2C=O$
Nucleophile $R'-NH_2$ (Primary Amine)
Functional Group formed $C=N$ (Imine linkage)

Final Solution: A Schiff's base is an imine characterized by the formula $R_2C=N-R'$, formed by the condensation reaction between a primary amine and an aldehyde or ketone with the loss of a water molecule, as exemplified by the reaction of benzaldehyde and aniline to yield N-benzylideneaniline.


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