In contrast to the addition of Br₂ the addition of HBr [Section 8.3] is not stereospecific. Why?

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br₂ (ii) Cl₂

(f)

Predict the product of the following haloalkane syntheses.

(a)

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.

(c)

In spite of being mechanistically similar to some of the reactions we saw in Chapter 8, rearrangement never occurred here in Chapter 9. Why doesn't rearrangement occur in the following bromination reaction despite the proximity of a more substituted carbon?

Show how each of the following compounds can be synthesized from an alkene:

b.

How does the first step in the reaction of propene with Br₂ differ from the first step in the reaction of propene with HBr?

To understand why Br⁻ adds to a carbon of the bromonium ion rather than to the positively charged ­bromine, draw the product that would be obtained if Br⁻ did add to bromine.

What is the product of the addition of I—Cl to 1-butene? (Hint: Chlorine is more electronegative than iodine [Table 1.3].)