GRE Subject Test: Chemistry : Electrophilic Addition

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

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Example Questions

Example Question #1 : Electrophilic Addition

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

Possible Answers:

Hexylcyclohexane

Cyclohexane

2-hexylcyclohexanol

3-hexylcyclohexanol

1-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.

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