Chapter 16, Problem 16.91P

Androsterone is a male sex hormone that controls the development of secondary sex characteristics in males. Draw the organic products formed when androsterone is treated with each reagent.

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

b. ${\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$

c. ${\text{CH}}_{\text{3}}\text{OH}$ (2 equivalents), ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$

d. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{OH}$ (2 equivalents), ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$