Question

The simplest method to convert an alcohol to an alkyl halide is by reacting the alcohol with concentrated HCl, HBr, or HI. Complete the mechanism and draw the intermediates and final products for the reaction of 1,3-dimethylcyclohexanol with concentrated HCl. Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the grid and connecting them with bonds, including charges where needed. Indicate the mechanism by drawing the electron-flow arrows on the molecules. Arrows should start on an atom or a bond and should end on an atom, bond, or where a new bond should be created.

Answer 1

The reaction of 1,3-dimethylcyclohexanol with concentrated HCl results in the formation of 1,3-dimethylcyclohexyl chloride.

Step-by-step explanation:

The reaction of 1,3-dimethylcyclohexanol with concentrated HCl involves the conversion of the alcohol group (-OH) into an alkyl halide group (-Cl). The mechanism for this reaction is known as an acid-catalyzed substitution. Here is the step-by-step mechanism:

1. The HCl molecule acts as the acid catalyst by protonating the alcohol group of the 1,3-dimethylcyclohexanol, resulting in the formation of a hydronium ion (H3O+) and a leaving group (Cl-).
2. The hydronium ion then attacks the C-O bond, leading to the formation of a carbocation intermediate.
3. The chloride ion (Cl-) then acts as the nucleophile, attacking the carbocation and forming a new C-Cl bond.

The final product of the reaction is 1,3-dimethylcyclohexyl chloride.