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The Wittig Reaction: Generation, Observation and Reactivity of a Phosphorous Ylide Intermediate. An Experiment for the Advanced Organic Chemistry Laboratory Course
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Abstract
An experiment has been devised that illustrates three important concepts in organic chemistry: the synthesis of an alkene via the Wittig reaction, characterization of a reactive intermediate by 1H NMR, and site - specific deuterium labelling. Deprotonation of ethyltriphenylphosphonium iodide (1) by methylsulfinyl carbanion (generated in situ by the reaction of NaH with DMSO-d6) results in the formation of the ylide, CH3CH-PPH3(2 -H). An ensuing, rapid deuterium exchange process between the deuterated solvent, and 2-H at the C-1 position affords CH3CD - PPH3 (2-D). The 1H NMR spectrum of 2-D was obtained, and the ylide was quenched with benzophenone to obtain 2-deutero-diphenylpropene (3) in 42% yield.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
SynthesisCiting Articles
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
Exploring the Stereochemistry of the Wittig Reaction: The Unexpected Influence of a Nominal Spectator Ion
John Hanson, Bill Dasher, Eric Scharrer and Tim HoytJournal of Chemical Education2010 87 (9), 971-974Exploring the Stereochemistry of the Wittig Reaction: The Unexpected Influence of a Nominal Spectator Ion
John Hanson, Bill Dasher, Eric Scharrer and Tim HoytJournal of Chemical Education2010 87 (9), 971-974Students in the second-semester organic chemistry laboratory perform a Wittig reaction between butylidenetriphenylphosphorane (an ylide) and benzaldehyde and determine the relative percentages of the cis and trans isomers of the 1-phenyl-1-pentene ...
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment
Sam H. Leung and Stephen A. AngelJournal of Chemical Education2004 81 (10), 1492Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment
Sam H. Leung and Stephen A. AngelJournal of Chemical Education2004 81 (10), 1492In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as ...
Wittig Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl trans-Cinnamate
Traci J. Speed , Jean P. McIntyre and Dasan M. ThamattoorJournal of Chemical Education2004 81 (9), 1355Wittig Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl trans-Cinnamate
Traci J. Speed , Jean P. McIntyre and Dasan M. ThamattoorJournal of Chemical Education2004 81 (9), 1355The synthesis of ethyl trans-cinnamate, by the reaction of benzaldehyde with the stabilized phosphorus ylid (carbethoxymethylene)triphenylphosphorane, serves as a useful experiment to illustrate the Wittig reaction in the introductory organic chemistry ...
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- Received: August 03, 2009
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