Skip to content
Question 59 of 66

Q.The formation of cyanohydrin from acetone is an example of :

(a) electrophilic addition
(b) nucleophilic substitution
(c) nucleophilic addition
(d) electrophilic substitution
Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2024MCQ· 1mImportance★★★★★
89% · 59/66 Questions
🔒 Locked · start free trial →

You're viewing a preview — the full solution, concept, methods & PYQ mapping are locked.

Start your 14-day free trial to unlock the full solution →

The cyanide ion is a nucleophile that adds directly across acetone's polarised carbonyl double bond (no group is displaced), giving the addition product cyanohydrin — a textbook nucleophilic addition, typical of the carbonyl group's reactivity.

Acetone's carbonyl carbon is electrophilic (partial positive charge, due to oxygen's higher electronegativity polarising the C=OC=O bond). The cyanide ion, CN−CN^- (generated from HCN with a trace of base/KCN), is a good nucleophile that attacks this electrophilic carbon; the pi electrons of the C=OC=O bond shift onto oxygen, and after protonation of the resulting alkoxide, the tetrahedral addition product — 2-hydroxy-2-methylpropanenitrile (acetone cyanohydrin) — is formed: CH3COCH3+HCN→(CH3)2C(OH)CNCH_3COCH_3 + HCN \rightarrow (CH_3)_2C(OH)CN This is a nucleophilic addition (not substitution, since no leav …

Unlock everything free for 14 days

  • Full step-by-step solutions
  • Concept-first explanations
  • Methods, shortcuts & mistakes
  • PYQ mapping + timed mock tests

Full access for 14 days. No credit card required.