Addition of Cl–OH to E-?-methylstyrene (1) results in the products shown below.

Question

Addition of Cl–OH to E-?-methylstyrene (1) results in the products shown below. Which of the following is the best explanation of that observation?

Select one:

a. The chloronium ion is unsymmetrical in this case so all four stereoisomers form.

b. The regiochemistry is inverted due to the steric bulk of the phenyl group.

c. A benzylic carbocation is an intermediate.

d. Rotation around the single bond in the products scrambles the stereochemistry.

e. The reaction is reversible and a thermodynamically controlled mixture of products results.

Explanation / Answer

Reaction of E-beta-methylstyrene with Cl-OH reagent proceeds via benzylic carbocation in the first step. The carbocation alpha to Ph ring is more stable and thus the product from it is formed by attack of OH- to this carbocation center.

c. A benzylic carbocation is an intermediate

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