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When a mixture containing one mole each of the three dimethylbenzenes (o-, m-, and p-xylene) is...

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When a mixture containing one mole each of the three dimethylbenzenes (o-, m-, and p-xylene) is treated with one mole of chlorine in the presence of a Lewis acid catalyst, one of the three hydrocarbons is monochlorinated in 100% yield, whereas the other two remain completely untouched.

a. Which isomer reacts? (m-zylene, o-zylene, or p-zylene?)

b. Draw the product expected.

c. The same experiment carried out on a mixture of the following three trimethylbenzenes gives a similar outcome. Draw the product of the one benzene that reacts.

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