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Problems and exercisesElectrophilic Addition of Halogens

1. Intramolecular bromine and double elimination

Predict the result of the following reactions:

An unsaturated alcohol with Br₂ gives C₉H₁₇BrO; 1,2-dimethylcyclohexene with 1) Br₂ and 2) t-BuOK in t-BuOH gives C₈H₁₂

2. Cycloalkenes and the meso form

Explain why the reaction of cycloalkenes such as cyclobutene, cyclopentene or cyclohexene with Br2 never gives a meso form, but a racemic mixture.

3. Halohydrins

Give the product of the reaction of propene with Br2 in water and explain its regiochemistry.

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