How would you prepare the following substances from 2-cyclohexenone? More than one step may be needed.

a.

b.

c.

d.

One of the name reactions for ketone is the Wolf-Kishner reaction, where the reagent used is ${\mathbf{H}}_{\mathbf{2}}{\mathbf{NNH}}_{\mathbf{2}}$/KOH, and the conversion of the ketone to alkane is observed.The reagent used for unsaturated ketones is the Gilman reagent, where the conjugate addition to $\alpha$,$\beta$ unsaturated ketones happens.

Wolff-Kishner reaction

Addition of Gilman reagent to cyclohexanone

Addition of Gilman reagent and oxidation with${\text{KMnO}}_{\text{4}}$

The first reaction is the addition of Gilman reagent in cyclohexanone, and then the compound formed undergoes the Wolff-Kishner reaction, where the ketone group is converted into an alkane.

The second reaction is the Wittig reaction, where the ketone group is converted to an alkene. After this, the compound formed undergoes reduction by ${\text{H}}_{\text{2}}\text{,Pd/C}$, both alkene groups present in a compound reduced to alkane.

Synthesis of 1-methylcyclohexane