All GRE Subject Test: Chemistry Resources
Example Questions
Example Question #2 : Reaction Mechanisms
What is the product of a hydroboration–oxidation reaction with 1-hexylcyclohexene?
Possible Answers:
Cyclohexane
Hexylcyclohexane
1-hexylcyclohexanol
3-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.
Yongmao
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Nankai University, Bachelor of Science, Chemistry. Washington University in St Louis, Doctor of Philosophy, Organic Chemistry.
All GRE Subject Test: Chemistry Resources
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