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Q8.5(i):
Draw structures of the following derivatives. (i) The 2,4-dinitrophenylhydrazone of benzaldehyde

Solution :

Step 1: Chemical Foundations and Component Identification

To determine the structure of the 2,4-dinitrophenylhydrazone of benzaldehyde, we analyze the condensation reaction between a carbonyl compound (benzaldehyde) and a derivative of hydrazine (2,4-dinitrophenylhydrazine). [Per the mechanism of nucleophilic addition-elimination in carbonyl compounds].

  • Benzaldehyde: $C_6H_5CHO$
  • 2,4-Dinitrophenylhydrazine (2,4-DNP): $H_2N-NH-C_6H_3(NO_2)_2$

The reaction occurs via the elimination of a water molecule ($H_2O$) between the carbonyl oxygen of benzaldehyde and the terminal amine group of the hydrazine derivative.

Step 2: Structural Derivation

The resulting product, 2,4-dinitrophenylhydrazone, retains the phenyl group from the benzaldehyde and the dinitrophenyl group from the reagent, joined by a double bond between the carbon and nitrogen atom ($C=N$).

Chemical formula of the product: $C_6H_5-CH=N-NH-C_6H_3(NO_2)_2$.

Step 3: Visual Representation

Ph CH N-NH C6H3 -NO2 -NO2

Step 4: Analytical Summary of the Molecular Structure

Component Description
Parent Carbonyl Benzaldehyde ($C_6H_5CHO$) providing the benzylidene moiety.
Functional Group Hydrazone linkage ($C=N-NH-$).
Substituents Two nitro ($-NO_2$) groups at the 2 and 4 positions of the phenyl ring attached to the nitrogen.

Final Solution: The structure of the 2,4-dinitrophenylhydrazone of benzaldehyde is $C_6H_5-CH=N-NH-C_6H_3(NO_2)_2$, characterized by the conjugation of the benzaldehyde phenyl ring with the dinitrophenylhydrazine moiety via the $C=N$ imine bond.


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