Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.
d. trans-2-methylcyclohexanol

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(m)

The bulky borane 9-BBN was developed to enhance the selectivity of hydroboration. In this example, 9-BBN adds to the less hindered carbon with 99.3% regioselectivity, compared with only 57% for diborane.

b. 9-BBN is synthesized by adding BH₃ across a symmetric, cyclic diene. What is the structure of the diene?

Show how you would accomplish the following synthetic conversions.

(b) but-1-ene → butan-2-ol

Show how you would synthesize the following alcohol from appropriate alkene.

(b)

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?