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ERIC Number: EJ1113955
Record Type: Journal
Publication Date: 2016-Sep
Pages: 6
Abstractor: As Provided
ISSN: ISSN-0021-9584
Water Mediated Wittig Reactions of Aldehydes in the Teaching Laboratory: Using Sodium Bicarbonate for the in Situ Formation of Stabilized Ylides
Kelly, Michael J. B.; Fallot, Lucas B.; Gustafson, Jeffrey L.; Bergdahl, B. Mikael
Journal of Chemical Education, v93 n9 p1631-1636 Sep 2016
The synthesis of alkenes using the Wittig reaction is a traditional part of many undergraduate organic chemistry teaching laboratory curricula. The aqueous medium version of the Wittig reaction presented is a reliable adaptation of this alkene formation reaction as a very safe alternative in the introductory organic chemistry laboratory. The specific aqueous Wittig reactions discussed use a "one-pot" reagent setup and greener methods that the students can complete within 30 min with partial workup in one laboratory period. The aqueous Wittig reactions presented have been implemented to various aldehydes and take advantage of dilute sodium bicarbonate ("baking soda") as the only base needed for in the in situ formation of stabilized ylides. Outcomes from the implementation of the proposed aqueous Wittig procedure into the organic chemistry teaching laboratory curriculum are presented. Described also are reaction workup, purification, and analysis of products using [superscript 1]H NMR and IR spectroscopy.
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:; Web site:
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Identifiers - Location: California (San Diego)
Grant or Contract Numbers: N/A