Why in Nucleophilic addition-elimination reactions,does the $C = O$ $C=O$ bond break when the nucleophile is added and not the $C - C L$ $C-CL$ bond ?

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Why in Nucleophilic addition-elimination reactions,does the $C = O$ $C=O$ bond break when the nucleophile is added and not the $C - C L$ $C-CL$ bond ?

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Answer 1 · 2016-11-21T18:05:41

I take it you refer to nucleophilic attack on an $acyl halide$ $"acyl halide"$ ?

Explanation:

$Reaction: N u^{-} + C l (O =) C R \to (N u) (^{-} O) (C l) C R \to N u (O =) C R + C l^{-}$ $"Reaction: " Nu^(-) + Cl(O=)CRrarr(Nu)(""^(-)O)(Cl)CRrarr Nu(O=)CR +Cl^-$

The carbonyl is presumed to stabilize the negative charge of the nucleophile, presumably by resonance. The ipso carbon is thus 4-coordinate, and we could trap such an intermediate by quenching with, say, $M e_{3} S i C l$ $Me_3SiCl$ to give $(N u) (M e_{3} S i O) (C l) C R$ $(Nu)(Me_3SiO)(Cl)CR$ .

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Why in Nucleophilic addition-elimination reactions,does the $C = O$ $C=O$ bond break when the nucleophile is added and not the $C - C L$ $C-CL$ bond ?

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Why in Nucleophilic addition-elimination reactions,does the C=OC=O bond break when the nucleophile is added and not theC−CLC-CL bond ?

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Why in Nucleophilic addition-elimination reactions,does the $C = O$ $C=O$ bond break when the nucleophile is added and not the $C - C L$ $C-CL$ bond ?