Question:

Which of the following compounds will not undergo Friedel Craft’s reaction with benzene ?

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Friedel-Crafts needs a carbocation or acylium ion; vinyl chloride cannot give a stable vinyl cation.
Updated On: Nov 11, 2026
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The Correct Option is B

Solution and Explanation

The options are: (1) acryloyl chloride \(\mathrm{CH_2{=}CH{-}COCl}\), (2) vinyl chloride \(\mathrm{CH_2{=}CH{-}Cl}\), (3) allyl chloride \(\mathrm{CH_2{=}CH{-}CH_2Cl}\), (4) methacryloyl chloride \(\mathrm{CH_2{=}C(CH_3){-}COCl}\).
Friedel-Crafts acylation works with the acid chlorides (1) and (4), which give acylium ions; alkylation works with allyl chloride (3), which gives a resonance-stabilised allyl carbocation.
Vinyl chloride (2) has a C-Cl bond with partial double-bond character (lone pair delocalisation) and would give an unstable vinyl cation, so it does not undergo Friedel-Crafts reaction with benzene.
Answer: (2) option (2) as drawn
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