Contact Information

Author
  • Andy Dicks
  • Senior Lecturer
  • Chemistry
  • Univ. of Toronto
  • 80 St. George Street
  • Toronto, ON
  • M5S 3H6
  • Canada
Email
Phone
(416) 946 - 8003
Website

Aqueous Horner-Wadsworth-Emmons Preparation Of A Sunscreen Analog

Laboratory Procedure (PDF)

Author Contact: adicks@chem.utoronto.ca

Summary

This experiment features the rapid and straightforward preparation of a sunscreen analog by a Horner-Wadsworth-Emmons reaction in water. Performed at the mid-undergraduate level, students use environmentally benign potassium carbonate as a base in an aqueous medium to synthesize and purify cinnamate esters. This strategy introduces a significant reduction in reaction time compared to previous pedagogical experiments, facilitates recognition of the role water plays as a solvent for organic reactions and provides a springboard for discussion of other green chemistry principles.

Summary prepared July 2008 by Andrew P. Dicks, Department of Chemistry at the University of Toronto.

Source

Cheung, L.; Lin, R. J.; McIntee, J. W.; Dicks, A. P. Chem. Educator [Online], Online 2005, 10, pp 300-302.

Chem. Educator [Online] Abstract

Category Descriptors

Chemistry Concepts
  • Aldehydes/Ketones
  • Aqueous Solution Chemistry
  • Carbonyl Chemistry
  • Esters
  • Stereochemistry
Laboratory Techniques
  • Assembly of Reaction Apparatus
  • IR Spectroscopy
  • Melting Points and Melting Ranges
  • Microscale Lab
  • NMR Spectroscopy
  • Recrystallization
  • UV-Vis Spectroscopy
Green Chemistry Principles
  • Design Less Hazardous Chemical Syntheses
  • Use Safer Solvents/Reaction Conditions
Chemistry Subdiscipline
  • Organic Chemistry
Target Audience
  • Colleges/Universities
Source
  • Journal Articles