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A Flexible Solvolysis Experiment for the Undergraduate Organic Laboratory

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John J. Esteb , John R. Magers , LuAnne McNulty , Paul Morgan , Kathryn Tindell and Anne M. Wilson

Department of Chemistry, Butler University, Indianapolis, IN 46208

J. Chem. Educ., 2009, 86 (7), p 853

DOI: 10.1021/ed086p853

Publication Date (Web): July 1, 2009

Section:

History, Education, and Documentation

Abstract

A simple S_N1 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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Alcohols

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

The Study of Substitution and Elimination Reactions Using Gas Chromatography: An Examination of the Effects of Alkane and Base Structure on Product Distributions
Donald L. Wharry
Journal of Chemical Education2011 88 (12), 1720-1723
- The Study of Substitution and Elimination Reactions Using Gas Chromatography: An Examination of the Effects of Alkane and Base Structure on Product Distributions
  Donald L. Wharry
  Journal of Chemical Education2011 88 (12), 1720-1723
  An experiment that compares product distribution obtained by either substitution or elimination utilizing alkyl bromides and methoxide, ethoxide, or t-butoxide as the base (or nucleophile) is described. The change in product distribution caused by steric ...
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