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Problems and exercisesAlkylarenes

1. Side-chain reactions

Give the product of the reaction of ethylbenzene with: a) NBS and light; b) hot KMnO4 and then H3O+; c) Br2/FeBr3.

2. Solvolysis

Why does benzyl chloride, a primary halide, react with water much faster than 1-chloropropane?

3. Acidity of toluene

The pKa of toluene is 41 and that of methane about 50. Why is toluene more acidic? Which base can deprotonate it?

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