Chemistry Aldehydes & Ketones MDCAT 2019
PMDC Verified Question 62 of 94
Which type of reaction takes place when a carbonyl compound is treated with a mixture of \( NaCN \) and an acid?
A
Electrophilic addition reaction
B
Displacement reaction
C
Nucleophilic addition reaction
D
Substitution reaction
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option C: Nucleophilic addition reaction
Concept:

The reaction mechanism depends on the polarity of the substrate and the nature of the attacking reagent.

Solution:

  • A mixture of \( NaCN \) and an acid generates Hydrogen Cyanide (\( HCN \)) in situ, which provides the strong nucleophile, \( CN^- \).


  • The carbonyl carbon is highly electrophilic due to the electron-withdrawing oxygen atom.


  • The \( CN^- \) nucleophile attacks this carbon, breaking the \( C=O \) pi bond and adding completely to the molecule to form a cyanohydrin.


  • Thus, the mechanism is a Nucleophilic addition reaction.


Why other options are incorrect:

Electrophilic addition is typical of non-polar double bonds (alkenes). Substitution requires a leaving group to depart, which does not happen here (the oxygen stays attached).

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