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ERIC Number: EJ960370
Record Type: Journal
Publication Date: 2011-Dec
Pages: 4
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
The Study of Substitution and Elimination Reactions Using Gas Chromatography: An Examination of the Effects of Alkane and Base Structure on Product Distributions
Wharry, Donald L.
Journal of Chemical Education, v88 n12 p1720-1723 Dec 2011
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 effects of the base and substrate are readily apparent. Prior work on this experiment focused on only the olefin products using a method without internal standards. The experiment examines all ether and olefin products as well as starting material and illustrates key principles of S[subscript N]2-S[subscript N]1 and E2-E1 reactions. For this experiment, a gas chromatographic method was developed that allows for complete product analysis. The new method examines the product distributions as a function of primary, secondary, and tertiary alkylbromide and base structure and can be expanded to include the interpretation of gas chromatographic data. Relative response factors were developed for the ether versus olefin products. If desired, the data in the supporting information can be utilized for in-class problems pertaining to substitution and elimination reactions. (Contains 3 tables and 5 figures.)
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A