Contact Information

Author
  • David Gonzalez
  • Assoc. Professor
  • Organic Chemistry
  • Departamento de Química Orgánica
  • Facultad de Química
  • Montevideo, Uruguay
Email
Phone
(5982) 9290106
Website

Enantioselective Reduction by Crude Plant Parts: Reduction of Benzofuran-2-yl Methyl Ketone with Carrot (Daucus carota) Bits

Author Contact: davidg@fq.edu.uy

Summary

Biocatalysis and biotransformations are important alternatives to consider when one is looking to substitute a conventional method with a greener one. One of the many advantages of using biotransformation as a synthetic method is that they are usually done in water and at ambient conditions. In addition, the reagents themselves are readily available, safe, and inexpensive to both buy and dispose of.

This experiment uses shredded carrots to enantioselectively reduce benzofuran-2-yl methyl ketone, yielding the optically pure alcohol. This lab illustrates the topics of green chemistry, biocatalysis, biotransformations, reductions, carbonyl chemistry, stereochemistry, stereoselectivity, optical activity, thin-layer chromatography, liquid-liquid extractions, and column chromatography.

The authors also suggest that students perform the sodium borohydride reduction of the ketone to compare and contrast the ease, safety, "greenness" and stereoselectivity of the two reactions.

The supplemental materials include lab procedures, lab report outline, lab questions, instructor notes, a list of necessary lab equipment, and CAS numbers.

Summary prepared October 2008 by Douglas M. Young at the University of Oregon.

Source

Ravía, S.; Gamenara, D.; Schapiro, V.; Bellomo, A.; Adum, J.; Seoane, G.; Gonzalez, D. J. Chem. Educ., Print 2006, 83, pp 1049-1051.

J. Chem. Educ. (Abstract only)

Category Descriptors

Chemistry Concepts
  • Aldehydes/Ketones
  • Aqueous Solution Chemistry
  • Carbonyl Chemistry
  • Enzyme Reactions
  • Enzymes
  • Natural Products
  • Oxidation/Reduction Chemistry
  • Stereochemistry
Laboratory Techniques
  • Extraction
  • Extraction and Drying Agents
  • Microscale Lab
  • NMR Spectroscopy
  • Optical Activity and Polarity
  • Rotary Evaporation
  • Thin-layer Chromatography
Green Chemistry Principles
  • Design Less Hazardous Chemical Syntheses
  • Minimize the Potential for Accidents
  • Use Renewable Feedstocks
  • Use Safer Solvents/Reaction Conditions
Chemistry Subdiscipline
  • Biochemistry
  • Organic Chemistry
Target Audience
  • Colleges/Universities
Source
  • Journal Articles