Chapter 29, Problem 41P

Draw the products formed when cholesterol is treated with each reagent. Indicate the stereochemistry around any stereogenic centers in the product.

a. ${\text{CH}}_{\text{3}}\text{COCl}$

b. ${\text{H}}_{\text{2}}$, $\text{Pd}$

c. PCC

d. oleic acid, ${\text{H}}^{+}$

e. [1] ${\text{BH}}_{\text{3}}$ THF; [2] ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$, ${\text{OH}}^{-}$