Starting from testosterone (Problem 17-62), how would you prepare the following substances?

a.

b.

c.

d.

a. In testosterone, there is one secondary alcohol present. By looking at the compound we are preparing, only the secondary alcohol group is converted to the ketone group. Here, the jones oxidation occurs when the secondary alcohol is oxidized to ketone by using chromic trioxide (oxidizing agent) and acid in water. Thus, the reagent used for the oxidation of secondary alcohol is ${\text{CrO}}_{\text{3}}$,${\text{H}}_{\text{3}}{\text{O}}^{+}$ . The reaction is as follows,

b. By looking at the compound (b), only the ketone group is converted to secondary alcohol, and other groups remain as it is. The ketone reduction to secondary alcohol is made by using ${\text{LiAlH}}_{\text{4}}$(a reducing agent) in the first step and acid in water in the second step. The reaction is as follows,

c. When we compare the testosterone compound with compound (c), we see the alkene group reduced to an alkane, and the secondary alcohol is converted to a ketone. So, in the first step, the reduction of alkene to alkane is made by using ${\text{H}}_{\text{2}}$, Pd/C (reducing agent). In the second step, the oxidation of secondary alcohol to a ketone is done using ${\text{CrO}}_{\text{3}}$,${\text{H}}_{\text{3}}{\text{O}}^{+}$ (oxidizing agent). Thus, the reaction is as follows,

d. When we compare the testosterone compound with compound (d), we see the alkene group reduced to an alkane, and the ketone is converted to alcohol. So, in the first step, alkene reduction to alkane is made by using ${\text{H}}_{\text{2}}$, Pd/C (reducing agent). In the second step, the reduction of the ketone to alcohol is made by using${\text{LiAlH}}_{\text{4}}$ (a reducing agent) and acid in water. Thus, the reaction is as follows,