Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.
(a)

Show how you would make the following compounds from a suitable cyclic alkene.

(d)

Show how you would accomplish the following synthetic conversions.

a. 3-methylpent-2-ene → 2-chloro-3-methylpentan-3-ol

Problem-Solving Hint: The opening of a halonium ion is driven by its electrophilic nature. The weak nucleophile attacks the carbon bearing more positive charge.

Predict the product of formula C₇H₁₃BrO from the reaction of this same unsaturated alcohol with bromine. Propose a mechanism to support your prediction.

Suggest an alkene that could be used to make each of the following halohydrins.

(a)

Provide arrow-pushing mechanisms for Assessments 9.10(b) and 9.10(c) that rationalize the regioselective and stereospecific formation of each halohydrin.

(b)

(c)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O

(d)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl₂, CH₃OH

(d)