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ArticuloA Multistep Synthesis Incorporating A Green Bromination of An Aromatic Ring
ArticuloA Multistep Synthesis Incorporating A Green Bromination of An Aromatic Ring
ArticuloA Multistep Synthesis Incorporating A Green Bromination of An Aromatic Ring
pubs.acs.org/jchemeduc
Laboratory Experiment
HAZARDS
Acetic anhydride and acetic acid are corrosive and can cause
burns. Aniline is harmful if inhaled. Acetone, acetic acid,
ethanol, and acetic anhydride are ammable. Sodium
hypochlorite is an oxidizing agent and can release toxic fumes
and should be used in a fume hood. Appropriate eye protection,
gloves, and a lab coat should be worn in order to avoid
chemical burns and contact with eyes and skin.
EXPERIMENTAL PROCEDURE
Protecting Aniline
Laboratory Experiment
ACKNOWLEDGMENTS
We would like to thank the CHEM 2220 students (winter 2010
and summer 2011 term) at the University of Manitoba for their
input concerning the experiment. As well, we would like to
thank Kirk Marat for use of the University of Manitoba NMR
facilities.
REFERENCES
CONCLUSION
This article describes an easy and safe multistep reaction for
demonstrating the use of a protecting group, an electrophilic
aromatic substitution reaction, and how redox reactions can be
used in organic chemistry. The products are solids and,
therefore, are easy for the students to manipulate for
purication. A variety of laboratory techniques are exercised
in this experiment: recrystallization, redox titration, IR and
NMR spectroscopy, and vacuum ltration. This experiment
also reinforces lecture material regarding nucleophilic acyl
substitution, benzene-ring substituent directing eects, redox
reactions, multistep synthesis, and protecting groups. Additionally, the procedure demonstrates to students that alternative
and safe pathways can be rationalized and developed that
accomplish an identical synthetic goal as traditional methods.
ASSOCIATED CONTENT
S Supporting Information
*
AUTHOR INFORMATION
Corresponding Author
*E-mail: luong@cc.umanitoba.ca.
Notes