Chemistry Aldehydes & Ketones MDCAT 2014
PMDC Verified Question 83 of 94
The structure of formula of the product of reaction of acetone with 2,4-dinitrophenyl hydrazine is:
A
\( (CH_3)_2CH-N(NH_2)-C_6H_3(NO_2)_2 \)
B
\( CH_3-CH=N-NH-C_6H_3(NO_2)_2 \)
C
\( (C_2H_5)_2C=N-NH-C_6H_3(NO_2)_2 \)
D
\( (CH_3)_2C=N-NH-C_6H_3(NO_2)_2 \)
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option D: \( (CH_3)_2C=N-NH-C_6H_3(NO_2)_2 \)
Concept:

Aldehydes and ketones react with 2,4-dinitrophenylhydrazine (2,4-DNPH) via a condensation reaction (nucleophilic addition followed by elimination of water) to form 2,4-dinitrophenylhydrazones.

Formula:

$$ (CH_3)_2C=O + H_2N-NH-Ar \longrightarrow (CH_3)_2C=N-NH-Ar + H_2O $$

Solution:

  • Acetone has the formula \( (CH_3)_2C=O \).


  • During the reaction, the oxygen atom from the carbonyl group of acetone and the two hydrogen atoms from the primary amine group of 2,4-DNPH are removed as a water molecule.


  • A new double bond forms between the carbonyl carbon and the nitrogen, giving the hydrazone structure \( (CH_3)_2C=N-NH-C_6H_3(NO_2)_2 \).


Why other options are incorrect:

Option B is the hydrazone of acetaldehyde. Option C is the hydrazone of 3-pentanone (diethyl ketone). Option A lacks the carbon-nitrogen double bond completely.

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