A Greener Bromination of Cyclohexene: An Organic Experiment for Non-majors

Demonstration Procedure (PDF)

Author Contact: mkerr@worcester.edu

Summary

Halogenation of alkenes is a classic reaction in organic chemistry, but is impractical to perform in the teaching laboratory due to toxicity and handling issues of the reagents. Bromination of cyclohexene utilizes the in situ generation of bromine from hydrobromic acid and hydrogen peroxide. For this particular experiment, all of the reagents are liquid, thus eliminating the need for a solvent. The small scale requires less complicated glassware and can be accomplished by students with less laboratory experience. Due to the visual nature of the experiment, it can also be used as a demonstration. This experiment was designed for use in college laboratories for non-majors and for high school advanced placement courses.

This experiment is a modification of "A Greener Bromination of Stilbene" (Green Organic Chemistry: Strategies, Tools, and Laboratory Experiments. Doxsee, K.M.; Hutchison, J.E. Thompson Learning: Mason, OH, 2002).

This experiment is available in both English and Vietnamese.

Summary prepared February 2007 by Margaret Kerr, Department of Chemistry at Worcester State College.

Category Descriptors

Chemistry Concepts

• Addition Rxn
• Alkenes

Green Chemistry Principles

• Design Less Hazardous Chemical Syntheses
• Maximize Atom Economy
• Minimize the Potential for Accidents
• Prevent Waste
• Use Safer Solvents/Reaction Conditions

Chemistry Subdiscipline

• Organic Chemistry

Target Audience

• Colleges/Universities
• Secondary Schools

Source

• Original Contributions - unpublished