The following haloalkanes can all be prepared starting from the same alkene. Give the alkene and the reagents needed for each.

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions:(ii) HCl

(k)

Imagine an electrophilic addition where the first step is exothermic. Which carbocation—2°, 3°, or neither—would you expect to form preferentially? Explain.

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(a)

Specify the conditions that would allow the synthesis of the 1° and 3° bromoalkanes from the same starting alkene.

Predict the product and provide a mechanism for the reaction of 1-methylcyclohexene with HBr.

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Provide a mechanism for the following reactions occurring with rearrangement.

(b)

Using an excess of HCl in the following reaction resulted in a product that was not simply the substitution of chlorine for the hydroxyl group. Predict the identity of the product obtained.

Provide an arrow-pushing mechanism that rationalizes the formation of each alkyl halide in Assessment 8.19.