Educational Materials for Organic Chemistry
Practice Questions for Chapter 5 - CEM 251
Following are some sample mechanism questions from chapter 5. Keep in mind that
the more time I spent discussing a mechanism in lecture, the more likely it is
to appear on the exam!Try drawing out answers to these problems and check your
answers with each other and/or any of your instructors. Solutions to these problems
will be available here approximately 1 week before the exam.
- Draw the mechanism for the addition of HCl to 1-methylcyclopentene. Refer to
the mechanism to explain (in 10 words or less) the regioselectivity of the reaction.
- Draw the mechanism for the addition of Br2 to cyclohexene. Refer to
the mechanism to explain (in 10 words or less) the stereochemistry of the reaction.
- Draw all correct Lewis structures (resonance structures) for the intermediate of
the reaction between 1-methylcycloheptene and Cl2 in the presence of water.
Use these structures to explain the regiochemistry (10 words or less) and the
stereochemistry (10 words or less) of the reaction.
- Draw the mechanism for the addition of HBr to 2-methyl-2-butene. Refer to the
mechanism to explain (in 10 words or less) the regioselectivity of the reaction.
Answer Mechanism Question 1
Answer Mechanism Question 2
Answer Mechanism Question 3
Answer Mechanism Question 4
Last modified 10/21/96
Abby Parrill
Department of Chemistry
Michigan State University
These pages may be downloaded and linked from other pages freely for
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parrill@argus.cem.msu.edu.