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CHM 252 Organic Chemistry II
Spring 2001
Workshop #3
- Complete the following reactions being sure to show ALL of the products that will form.
Work through all of the mechanisms being sure to highlight (explain) critical
features that ultimately control the progress of the reaction. Pay particularly close
attention to aspects of regiochemistry and stereochemistry.
- Explain why the following compound reacts to give a mixture of alkene isomers in which
only the Z isomer contains deuterium.
- Using the curved arrow formalism, provide a mechanism to explain each of the following
conversions.
- Acid-catalyzed dehydration of 2,2-dimethylcyclohexanol yields a mixture of
1,2-dimethylcyclohexene and isopropylidenecyclopentane (shown below). Propose reaction
mechanisms to account for the formation of both products. Which product do you think
represents the thermodynamic product? Explain.
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