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NEET CHEMISTRYAldehydes, Ketones and Carboxylic AcidsMedium

Question

The compound that is most susceptible to a nucleophilic attack in the carbonyl group is:

A

CH₃COOCH₃

B

CH₃CONH₂

C

CH₃COOCOCH₃

D

CH₃COCl

Step-by-Step Solution

The reactivity of carboxylic acid derivatives towards nucleophilic acyl substitution depends on the electrophilicity of the carbonyl carbon and the leaving group ability of the substituent.

The order of reactivity is: Acyl Halides (RCOCl) > Acid Anhydrides ((RCO)₂O) > Esters (RCOOR') > Amides (RCONH₂)

Reasons:

  1. Leaving Group Ability: The chloride ion (Cl−Cl^-) is a weaker base and thus a better leaving group than acetate (RCOO−RCOO^-), alkoxide (RO−RO^-), or amide (NH2−NH_2^-) ions.
  2. Inductive Effect: Chlorine has a strong electron-withdrawing (-I) effect, which increases the positive charge density on the carbonyl carbon, making it more susceptible to nucleophilic attack.
  3. Resonance: In amides and esters, strong resonance delocalization reduces the electrophilicity of the carbonyl carbon, making them less reactive.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Aldehydes, Ketones and Carboxylic Acids. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAldehydes, Ketones and Carboxylic Acidscompoundsusceptiblenucleophilicattackcarbonyl

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