Q.The formation of cyanohydrin from acetone is an example of :
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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 bond). The cyanide ion, (generated from HCN with a trace of base/KCN), is a good nucleophile that attacks this electrophilic carbon; the pi electrons of the bond shift onto oxygen, and after protonation of the resulting alkoxide, the tetrahedral addition product — 2-hydroxy-2-methylpropanenitrile (acetone cyanohydrin) — is formed: This is a nucleophilic addition (not substitution, since no leav …
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