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Question 52 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 2022MCQ· 1mImportance★★★★★
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The carbonyl carbon of acetone is electrophilic, so the nucleophilic CN−CN^- (from HCN) adds to it, and after protonation of the resulting alkoxide the C=OC=O double bond becomes a single bond bearing both −OH-OH and −CN-CN — an addition, driven by a nucleophile, not a substitution.

Acetone, (CH3)2C=O(CH_3)_2C=O, has a polarised carbonyl carbon (δ+\delta^+) due to the electronegative oxygen. The cyanide ion CN−CN^- acts as a nucleophile, attacking this carbon and adding across the double bond; protonation of the resulting alkoxide by HCN/H+H^+ gives the cyanohydrin, (CH3)2C(OH)CN(CH_3)_2C(OH)CN. Because a nucleophile adds to (rather than substitutes at) an unsaturated carbon, with no leaving group d …

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