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The Electrophilic Bromination of Toluene: Determination of the Ortho, Meta, and Para Ratios by Quantitative FTIR Spectrometry

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Ross E. Smith IV, James R. McKee and Murray Zanger

Department of Chemistry & Biochemistry, University of the Sciences in Philadelphia, Philadelphia, PA 19104-4495

J. Chem. Educ., 2002, 79 (2), p 227

DOI: 10.1021/ed079p227

Publication Date (Web): February 1, 2002

Section:

History, Education, and Documentation

Abstract

The bromination of toluene is used to illustrate the principles of electrophilic aromatic substitution. The products of the microscale synthesis are analyzed using quantitative IR spectroscopy. The experiment is simple to carry out and gives an accurate analysis of the ortho-, meta-, and para-bromotoluenes in the product mixture. The relative reactivities of the ortho, meta, and para protons can also be calculated.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Analytical Chemistry

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Instrumental Methods

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