JCE Online Journal of Chemical EducationDivision of Chemical Education, American Chemical SocietyAmerican Chemical Society
 | Subscriptions  | Software Orders  | Support  | Contributors  | Advertisers  | 

JCE Print
   Current Issue
 Previous Issues
 Supplements
 Search JCE Index

JCE Digital Library
   JCE DLib Catalog
   ChemInfo
 Data-Driven Exercises
 DigiDemos
 Featured Molecules
 LivTexts
 LrnCom
 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
 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 > 2009  > July  >
In the Laboratory
A Flexible Solvolysis Experiment for the Undergraduate Organic Laboratory
John J. Esteb, John R. Magers, LuAnne McNulty, Paul Morgan, Kathryn Tindell, and Anne M. Wilson
Department of Chemistry, Butler University, Indianapolis, IN 46208
Cover
July 2009
Vol. 86 No. 7
p. 853
Abstract
A simple SN1 reaction is presented that uses bromotriphenylmethane and a range of oxygen-based nucleophiles including water and various alcohols. This procedure represents a process that affords easy isolation of solid products. Typical student yields ranged from 17–128% with the average yield of 50%. Students obtained products with a melting point range of 140 to 164 °C. This procedure offers multiple ways to adapt this experiment from a straight solvolysis reaction to a discovery-based experiment that explores the effect of nucleophile (for a more advanced group) or the method of product isolation.
Supplement
Student handout including pre- and postlaboratory questions; Instructor notes including the answers to the pre- and postlaboratory questions and the NMR and IR spectra
*
 Download
Contents
  JCE2009p0853W.pdf
 
 
More Information
*
Citation
Esteb, John J.; Magers, John R.; McNulty, LuAnne; Morgan, Paul; Tindell, Kathryn; Wilson, Anne M. J. Chem. Educ. 2009, 86, 853.
*
Keywords
Alcohols; Carbocations; Ethers; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; NMR Spectroscopy; Nucleophilic Substitution; Organic Chemistry; Reactions; Second-Year Undergraduate; Synthesis
*
History
Created:
Last Updated:
6/1/2009
6/9/2009
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
<< Previous Article Table of Contents Next Article >>
  Home > JCE Print > Journal of Chemical Education > Issues > 2009  > July  > Page 853


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.