Question

Identify reagents necessary to convert cyclohexane into 1,3-cylohexadiene: notice that the starting material has no leaving groups and cannot simply be treated with a strong base. you must first introduce functionality into the starting material.

Answer 1

1,3-cylohexadiene i synthesized starting from cyclohexane in following 4 steps.

1) Free Radical Substitution Rxn: Halogenation of cyclohexane in the presence of UV yield chlorocyclohexane.

2) Elimination Rxn: Dehydrohalogenation of chlorocyclohexane yields cyclohexene.

3) Halogenation of Cyclohexene (Electrophillic Addition Rxn) gives 1,2-dihalocyclohexane.

4) Elemination Rxn: When dibromocyclohexane is treated with KOH and heated it gives 1,3-cyclohexadiene as shown below,