Question

Draw the structure of the chlorohydrin formed by treating 1 -methylcyclohexene with \(\mathrm{Cl}_{2} / \mathrm{H}_{2} \mathrm{O}\).

Short answer

Answer: The resultant structure of the chlorohydrin formed would have the hydrogen atom from water added to the carbon of the double bond containing two hydrogens, and the chlorine atom added to the carbon of the double bond containing one hydrogen, while maintaining the cyclohexane backbone and the methyl group.

Step-by-step solution

Identify the reaction

The reaction that is taking place is called hydrochlorination, which is the addition of water (H2O) and a halogen (Cl) to an alkene (1-methylcyclohexene) in the presence of Cl2.

Determine the regioselectivity of the reaction

According to Markovnikov's rule, during hydrochlorination of an alkene, the hydrogen atom (from water) will bond to the carbon with more hydrogen atoms, and the halogen will bond to the carbon with fewer hydrogen atoms. In the case of 1-methylcyclohexene, the hydrogen will bond to the carbon on the double bond that already has two hydrogens, while the chlorine will bond to the other carbon of the double bond, which has only one hydrogen currently.

Draw the final structure of the chlorohydrin

Following Markovnikov's rule, the final structure of the chlorohydrin will have the hydrogen atom from water added to the carbon of the double bond containing two hydrogens, and the chlorine atom added to the carbon of the double bond containing one hydrogen, while maintaining the cyclohexane backbone and the methyl group. The structure will be as follows: