GRE Subject Test: Chemistry : Electrophilic Addition

Study concepts, example questions & explanations for GRE Subject Test: Chemistry

varsity tutors app store varsity tutors android store

Example Questions

Example Question #31 : Reactions By Product

What is the product of a hydroboration–oxidation reaction with 1-hexylcyclohexene?

Possible Answers:

3-hexylcyclohexanol

Cyclohexane

Hexylcyclohexane

1-hexylcyclohexanol

2-hexylcyclohexanol

Correct answer:

2-hexylcyclohexanol

Explanation:

This reaction is an electrophilic addition reaction with an alkene. This is one of many alkene addition reactions that can add an -OH group onto your starting material. The key aspect of an hydroboration-oxidation reaction is the anti-Markovinikov addition to the double bond. The -OH group should be on the least substituted of the two carbons that originate from the double bond. In light of this information, the answer is 2-cyclohexanol.

Learning Tools by Varsity Tutors