Question

Draw a stepwise mechanism for the conversion of dihalide A and cyclohexane-1,4-diol to polyether B in the presence of AlCl₃.

Short answer

Answer

Mechanism of the reaction

Step-by-step solution

Dihalides

The organic compound that bears two halogen atoms is called dihalides. Some of the examples for dihalides are ethylene dichloride, 1,1-dichloroethane, 1,2-dibromoethane, etc.

Cyclohexane-1,4-diol

The cyclohexane ring that bears hydroxyl groups at the first and fourth carbon is cyclohexane-1,4-diol.The molecular formula of this compound is${\mathrm{C}}_6{\mathrm{H}}_{12}{\mathrm{O}}_2$ .

About the mechanism

The chlorine atom attacks AlCl₃ lead to the development of a positive charge on the chlorine atom and a negative charge on the aluminum atom. The carbocation will be developed by resonance stabilization.

Then this species is treated with cyclohexane-1,4-diol and some rearrangements are carried out. The resulting species is treated with HCl andAlCl₃ . The steps are repeated several times to get the desired polymer.

Mechanism of the reaction