JCE Online Journal of Chemical Education
 | Subscriptions  | Software Orders  | Support  | Contributors  | Advertisers  | 

JCE Print
   Current Issue
 Previous Issues
 Supplements
 Search JCE Index

JCE Digital Library
   DigiDemos
 QBank
 SymMath
 WebWare

JCE Software
   Latest Releases
 Software & Video
 Downloads
 Support

Only@JCE Online
   JCE Online Store
 JCE HS CLIC
 JCE Discussion Forums
   Biographical Snapshots
 ChemEd Resource Shelf
 Featured Molecules
 Hal's Picks
 Project Chemlab
 Reviewed WWW Sites
 "Web-Ed" Articles

About JCE
   Features
 Publications
 Operations
 Outreach
 Contact Us


  Home > JCE Print > Journal of Chemical Education > Issues > 2003  > June  >
Research: Science and Education
The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena
Joel Rosenthal and David I. Schuster
Department of Chemistry, New York University, New York, NY 10003
Cover
June 2003
Vol. 80 No. 6
p. 679
Abstract
Fluorobenzene (PhF) displays a reactivity in electrophilic aromatic substitution (EAS) that is, at first glance, anomalous in comparison to the reactivity of the other halobenzenes. This is borne out by the fact that the rates of typical EAS reactions on PhF, such as nitration and chlorination, are 15–80% as fast as that of benzene while the same reactions on the other halobenzenes are five to ten times slower than that of PhF. Most striking, however, is the fact that reactions at the para position of PhF are typically faster than the corresponding reactions at a single position of benzene. Furthermore, EAS on PhF results in ∼ 90% of the para-substituted product, while the other halobenzenes give ratios of ortho- and para-substituted products that are closer to the simple statistical distribution. These striking observations are not discussed or, for that matter, even reported in introductory or advanced textbooks of organic chemistry and are clearly not compatible with the typically superficial textbook discussions of this subject. New models incorporating the interplay of inductive stabilization and resonance effects involving fluorine can be used to explain not only these counterintuitive experimental observations but also other interesting facets of organofluorine chemistry.

See Letter re: this article.
More Information
*  Citation
 Rosenthal, Joel; Schuster, David I. J. Chem. Educ. 2003 80 679.
*  Keywords
 Fluorine; Organic Chemistry; Textbooks; Aromaticity / Aromatics; Mechanisms of Reactions; Organic Synthesis
*  History
 Created:
Last Updated:		 May 5, 2003
February 28, 2005
Link to Letter added (April 2004).
<< Previous Article Table of Contents Next Article >>
  Home > JCE Print > Journal of Chemical Education > Issues > 2003 > June > Page 679


Subscriptions
 Subscription Info
 Order Forms

JCE HS CLIC

Our Secondary School editors work hard to distill all the JCE materials to produce a fraction of particular interest to high school teachers. We call it CLIC.
 JCE HS CLIC

Contributions Welcome
JCE welcomes your submission
 Contributors' Corner

Advertisers
In recent years we have worked hard to better match our advertisers with our readers. When shopping for chemistry education materials, visit our advertisers' WWW sites first.
 Recent Advertisers

Be An Ambassador
Take JCE along on your outreach missions. Copies of the Journal, guest access to JCE Online, our publications catalog, and more are available for your participants.
 Outreach with JCE

Comments to
jceonline@chem.wisc.edu		 Copyright © Division of Chemical Education, Inc., American Chemical Society.
All rights reserved.