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Problems and exercisesortho-para Directors

1. Ortho-para groups

Predict the result of the following reactions:

Eight reactions: bromination of toluene, sulfonation of anisole, nitration of tert-butylbenzene, alkylation of ethylbenzene with cyclohexene, styrene with H₂SO₄, 1-phenylcyclohexene with Br₂ without and with FeBr₃, allylbenzene with H₂SO₄ and 4-phenylbutan-1-ol with BF₃

2. Ortho-para deactivators

Why do halogens deactivate the ring and yet direct to ortho and para?

3. Aniline in acidic medium

Nitration of aniline with HNO₃/H₂SO₄ gives substantial amounts of m-nitroaniline. Why? How is p-nitroaniline obtained?

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