Prev. Article Next Article Table of Contents

Article

C-H and C-D Bonds: An Experimental Approach to the Identity of C-H Bonds by Their Conversion to C-D Bonds

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Alex T. Rowland

Department of Chemistry, Gettysburg College, Gettysburg, PA 17325

J. Chem. Educ., 2003, 80 (3), p 311

DOI: 10.1021/ed080p311

Publication Date (Web): March 1, 2003

Abstract

Three experiments are described which experimentally verify concepts encountered by first-year organic chemistry students concerning the reactivity (acidity) of various types of hydrogens bonded to carbons. Two experiments involve the direct replacement of benzylic hydrogens by deuterium atoms upon treatment with acid or base in methanol-d. The third experiment involves a Michael reaction under basic conditions, resulting in the exchange of α hydrogens with no effect upon alkyl, aromatic, or benzyl hydrogens. The results of the deuterium exchange reactions are analyzed by IR and ¹H NMR spectroscopy. The experiments provide a vehicle to discuss the correlation of hydrogen reactivity, reaction mechanisms, and the use of spectroscopic methods.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Acids / Bases

View: Hi-Res PDF | PDF w/ Links

Citing Articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

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

The State of Organic Teaching Laboratories
Gail Horowitz
Journal of Chemical Education2007 84 (2), 346
- The State of Organic Teaching Laboratories
  Gail Horowitz
  Journal of Chemical Education2007 84 (2), 346
  This review explores the dramatic changes that have taken place in the organic chemistry laboratory course over the last two to three decades. The most significant changes have been in the areas of pedagogy and technology. Significant inroads have been ...
  Abstract | Hi-Res PDF | PDF w/ Links