Prev. Article Next Article Table of Contents

Lab-Expt

Wittig Reaction: The Synthesis of trans-9-(2-Phenylethenyl)anthracene Revisited

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

Purchase the full-text

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

Christine Jaworek and Sarah Iacobucci

Department of Chemistry, Tufts University, Medford, MA 02155

J. Chem. Educ., 2002, 79 (1), p 111

DOI: 10.1021/ed079p111

Publication Date (Web): January 1, 2002

Abstract

The revisit to this experimental procedure resulted in making a good undergraduate laboratory procedure even better. In this Wittig reaction, readily available starting materials are used; only the trans isomer is produced; the clear and characteristic ¹H NMR spectrum of the product is ideal for a lesson in coupling constants to determine stereochemistry; and the product can be readily used in additional brilliant chemiluminescence laboratory experiments. The problematic step of generating tough emulsions during extractions with halogenated solvents has been eliminated by using N,N-dimethylformamide as the reaction solvent and readily precipitating the product from the reaction mixture using 1-propanol and water.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Chromatography

View: Hi-Res PDF | PDF w/ Links

Citing Articles

View all 3 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 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 Hoyt
Journal of Chemical Education2010 87 (9), 971-974
- Exploring the Stereochemistry of the Wittig Reaction: The Unexpected Influence of a Nominal Spectator Ion
  John Hanson, Bill Dasher, Eric Scharrer and Tim Hoyt
  Journal of Chemical Education2010 87 (9), 971-974
  Students 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 ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment
Sam H. Leung and Stephen A. Angel
Journal of Chemical Education2004 81 (10), 1492
- Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment
  Sam H. Leung and Stephen A. Angel
  Journal of Chemical Education2004 81 (10), 1492
  In 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 ...
  Abstract | Hi-Res PDF | PDF w/ Links
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. Thamattoor
Journal of Chemical Education2004 81 (9), 1355
- 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. Thamattoor
  Journal of Chemical Education2004 81 (9), 1355
  The 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 ...
  Abstract | Hi-Res PDF | PDF w/ Links