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Which of the following reagents will convert benzene to isopropylbenzene? Choose all that are appropriate.

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I know for certain that (b) can be used, but I also think the following mechanism with (d) is also possible:

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Is my line of thinking correct with this one?

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You are right, both abstracting $\ce{Cl-}$ from the alkyl chloride with Lewis acid as well as dehydration of isopropanol with $\ce{H2SO4}$ are suitable ways to generate the 2-propyl carbocation, your electrophile in this reaction. Option (c) will not work because $\ce{AlCl3}$ reacts with alcohols to form aluminium alkoxides.

Source: Master Organic Chemisry

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  • $\begingroup$ Out of curiosity: wouldn't d) produce a significant amount of $\ce{PhSO3H}$ ? $\endgroup$ – permeakra May 19 '18 at 18:15

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