Contact Information

Author
  • James E. Hutchison
  • Professor
  • Chemistry
  • Univ. of Oregon
  • Eugene, OR 97403
Email
Phone
(541) 346 - 4228
Website

Electrophilic Aromatic Iodination of 4'-Hydroxyacetophenone

Laboratory Procedures (PDF)

Author Contact: hutch@uoregon.edu

Summary

Aromatic halogenation is an important tool for the conversion of aromatic compounds into specific compounds of interest or importance. This laboratory module investigates the iodination of 4'-hydroxyacetophenone using sodium iodine and household bleach (as an oxidizing agent) in aqueous ethanol. The reaction conditions used in this laboratory module offer two advantages over more traditional methods: (1) the reaction is efficient and selective leading to good yields of monoiodinated product and (2) the method offers more environmentally benign reaction conditions (less hazardous oxidizing agent - NaOCl vs. nitric acid and a relative benign solvent- ethanol). The link to the laboratory procedures includes pre- and -post lab questions.

Summary prepared May 2005 by Julie A. Haack, Department of Chemistry at the University of Oregon.

Source

Gilbertson, R.; Parent, K. E.; McKenzie, L. C.; Hutchison, J. E. Electrophilic Aromatic Iodination of 4'-Hydroxyacetophenone Greener Approaches to Undergraduate Chemistry Experiments, Print Kirchhoff, M., Ryan, M., Eds.; American Chemical Society: Washington D.C., 2002; pp 1-3.

Category Descriptors

Chemistry Concepts
  • Electrophilic Substitution
  • Oxidation/Reduction Chemistry
Laboratory Techniques
  • Assembly of Reaction Apparatus
  • Melting Points and Melting Ranges
  • Recrystallization
  • Rotary Evaporation
Green Chemistry Principles
  • Avoid Chemical Derivatives
  • Design Less Hazardous Chemical Syntheses
  • Use Safer Solvents/Reaction Conditions
Chemistry Subdiscipline
  • Organic Chemistry
Target Audience
  • Colleges/Universities
Source
  • Books