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  Home > JCE Print > Journal of Chemical Education > Issues > 2003  > March  >
In the Laboratory
C–H and C–D Bonds: An Experimental Approach to the Identity of C–H Bonds by Their Conversion to C–D Bonds
Alex T. Rowland
Department of Chemistry, Gettysburg College, Gettysburg, PA 17325
Cover
March 2003
Vol. 80 No. 3
p. 311
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.
Supplement
Detailed procedures for the preparation of dianisalacetone and the deuterium exchange reactions are available.
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*  Citation
 Rowland, Alex T. J. Chem. Educ. 2003 80 311.
*  Keywords
 Acid–Base Chemistry; IR Spectroscopy; Isotopes; Laboratory Instruction; NMR Spectrometry; Organic Chemistry; Undergraduate Research
*  History
 Created:
Last Updated:		 February 6, 2003
February 28, 2005
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