10. Addition Reactions

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

d. trans-2-methylcyclohexanol

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

a. borane in tetrahydrofuran, followed by basic hydrogen peroxide

Unlike hydroboration–oxidation, the addition of H₂O catalyzed by H₃O⁺ is not stereospecific. Thinking carefully about the mechanism of the reaction, give two reasons why.

Draw the products of the following reactions, including their configurations:

What reagents are needed to carry out the following syntheses?

Explain why, in hydroboration–oxidation, HO⁻ and HOOH cannot be added until after the hydroboration reaction is over.

Show how you would accomplish the following synthetic conversions.

c. 2-bromo-2,4-dimethylpentane → 2,4-dimethylpentan-3-ol

Show how you would accomplish the following transformations.

(c) 1-methylcycloheptanol → 2-methylcycloheptanol

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

k. BH₃/THF, followed by H₂O₂, HO^- , H₂O

Predict the products you would get when the following alkenes undergo (ii) oxymercuration–reduction [1. Hg(OAc)₂ , H₂O 2. NaBH₄ ].

(b)