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had the obsolete reaction tag, added carbocation and halide tags
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Fridel Crafts Friedel-Crafts Alkylation and hybridization

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Fridel Crafts Alkylation and hybridization

Why must the alkyl halide be sp3 hybridized with respect to the carbon connected to the halogen for the alkylation to occur?

Why, for example, can't we use acetylide with a bromine substituted for hydrogen on one side in conjunction with aluminum tribromide to alkylate benzene?

If anything this seems to be more favorable as an sp carbocation is likely less stable than an sp3 carbocation.