Chemistry Aldehydes & Ketones ETEA 2022
PMDC Verified Question 33 of 94
Acetone reacts with hydrogen cyanide (\( HCN \)) to form a cyanohydrin. It is an example of:
A
Electrophilic addition
B
Electrophilic substitution
C
Nucleophilic substitution
D
Nucleophilic addition
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option D: Nucleophilic addition
Concept:

The carbonyl group (\( C=O \)) features an electrophilic carbon atom due to the electronegative oxygen pulling the pi electrons away from it.

Solution:

  • In the reaction with \( HCN \), the attacking species is the cyanide nucleophile (\( CN^- \)).


  • The nucleophile attacks the partially positive carbonyl carbon, breaking the \( \pi \) bond and transferring the electrons onto oxygen.


  • Oxygen is subsequently protonated to form an alcohol group. Since two molecules (acetone and HCN) combine completely to form one molecule (a cyanohydrin) without any leaving group, the mechanism is a Nucleophilic addition.


Why other options are incorrect:

Electrophilic addition is typical of non-polar \( C=C \) bonds. Substitution reactions require an atom or group to leave, which does not happen in cyanohydrin formation.

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