10. Addition Reactions

What stereoisomers are obtained from the following reactions?

c. (E)-3-methyl-2-pentene + HBr

d. cis-3-hexene + HBr

a. Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.

b. Would both alkenes form the same alkyl halide if DBr were used instead of HBr? (D is an isotope of H, so D⁺ reacts like H⁺.)

Suggest an alkene that, upon reaction with the appropriate hydrohalic acid, will produce only the alkyl halide shown. [Ignore stereochemistry.]

(d)

What is the major product of each of the following reactions?

1.

What is the expected product for the reaction of each of the following alkenes with (i) HBr and (ii) HCl?

(d)

Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

1. HCl

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

(g)

Show how hex-1-yne might be converted to

e. 2-bromohexane.

Which of the following is the major product formed when $H_{\mathrm{Br}}$ reacts with 2-methyl-2-butene under standard conditions?

What is the major product of the reaction of each of the following with HBr?

c.

d.

Propose a mechanism for each of the following reactions:

b.

(a) How would you convert propene to 2-bromopropane?

Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.

g. 3,3-dimethyl-1-pentene + HBr

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.