10. Addition Reactions

Predict the product of the following reaciton.

Predict the product of the following reaction.

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

b.

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

b.

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

a.

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

e.

Which stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br₂ and H₂O?

Predict the major product(s) for each reaction. Include stereochemistry where appropriate.

c. cis-but-2-ene + Cl₂/H₂O

d. trans-but-2-ene + Cl₂/H₂O

Predict the major product(s) for each reaction. Include stereochemistry where appropriate.

a. 1-methylcyclohexene + Cl₂/H₂O

b. 2-methylbut-2-ene + Br₂/H₂O

Propose a mechanism for the addition of bromine water to cyclopentene, being careful to show why the trans product results and how both enantiomers are formed.

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.