Microwave-Assisted Synthesis of a Natural Insecticide on Basic Montmorillonite K10 Clay. Green Chemistry in the Undergraduate Organic Laboratory

Matthew R. Dintzner , Paul R. Wucka and Thomas W. Lyons
Department of Chemistry, DePaul University, Chicago, IL 60614
J. Chem. Educ., 2006, 83 (2), p 270
DOI: 10.1021/ed083p270
Publication Date (Web): February 1, 2006

Abstract

A microwave-assisted, one-pot synthesis of a naturally occurring insecticide on basic Montmorillonite K10 is described. The reaction is suitable for incorporation into the undergraduate organic chemistry laboratory course and represents a practical example of green chemistry. The described synthesis employs naturally benign, base-washed Montmorillonite K10 clay as a heterogeneous catalyst, is carried out under solvent-free conditions in a commercial-grade microwave oven, and features several interesting mechanistic considerations, including an electrophilic aromatic addition, dehydration, and intramolecular hetero-Diels–Alder cyclization.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

Green Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Chromatography

Citing Articles

View all 8 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 8 ACS Journal articles (5 most recent appear below).

  • Cover Image

    A Research-Based Undergraduate Organic Laboratory Project: Investigation of a One-Pot, Multicomponent, Environmentally Friendly Prins–Friedel–Crafts-Type Reaction

    Matthew R. Dintzner, Justin J. Maresh, Charles R. Kinzie, Anthony F. Arena, and Thomas Speltz
    Journal of Chemical Education2012 89 (2), 265-267
    • A Research-Based Undergraduate Organic Laboratory Project: Investigation of a One-Pot, Multicomponent, Environmentally Friendly Prins–Friedel–Crafts-Type Reaction

      Matthew R. Dintzner, Justin J. Maresh, Charles R. Kinzie, Anthony F. Arena, and Thomas Speltz
      Journal of Chemical Education2012 89 (2), 265-267

      Students in the undergraduate organic laboratory synthesize tetrahydro-2-(4-nitrophenyl)-4-phenyl-2H-pyran via the Montmorillonite K10 clay-catalyzed reaction of p-nitrobenzaldehye with methanol, 3-buten-1-ol, and benzene. The synthesis comprises an ...

  • Cover Image

    The Cyclohexanol Cycle and Synthesis of Nylon 6,6: Green Chemistry in the Undergraduate Organic Laboratory

    Matthew R. Dintzner, Charles R. Kinzie, Kimberly Pulkrabek, and Anthony F. Arena
    Journal of Chemical Education2012 89 (2), 262-264
    • The Cyclohexanol Cycle and Synthesis of Nylon 6,6: Green Chemistry in the Undergraduate Organic Laboratory

      Matthew R. Dintzner, Charles R. Kinzie, Kimberly Pulkrabek, and Anthony F. Arena
      Journal of Chemical Education2012 89 (2), 262-264

      A one-term synthesis project that incorporates many of the principles of green chemistry is presented for the undergraduate organic laboratory. In this multistep scheme of reactions, students react, recycle, and ultimately convert cyclohexanol to nylon 6,...

  • Cover Image

    Research Advances

    Angela G. King
    Journal of Chemical Education2010 87 (2), 123-127
    • Research Advances

      Angela G. King
      Journal of Chemical Education2010 87 (2), 123-127

      The Research Advances for February 2010 summarizes research on how plant hormones called brassinosteroids can help to activate plant pesticide metabolism, the presence of a virus fighter in “Devil’s dung,” how kudzu isoflavones might improve human health, ...

  • Cover Image

    Using Green Chemistry to Enhance Faculty Professional Development Opportunities

    Margaret E. Kerr and David M. Brown
    2009 1011 (), 19-36
    • Using Green Chemistry to Enhance Faculty Professional Development Opportunities

      Margaret E. Kerr and David M. Brown
      2009 1011 (), 19-36

      Of the plethora of benefits that derive from practicing green chemistry, one that is not often considered, or at least discussed, is its application toward enhancing the professional development of faculty as they advance through the ranks. Opportunities ...

  • Cover Image

    Green Chemistry Education: Toward a Greener Day

    Mary M. Kirchhoff
    2009 1011 (), 187-194
    • Green Chemistry Education: Toward a Greener Day

      Mary M. Kirchhoff
      2009 1011 (), 187-194

      Green chemistry began infiltrating the curriculum in the late 1990s, when several enterprising faculty members started introducing greener laboratory experiments, stand-alone courses, and green chemistry modules into their teaching. Widespread coverage of ...

Tools

SciFinder Links

SciFinder subscribers:  Click to sign in | Not a SciFinder subscriber? Learn more at www.cas.org

Explore by:


History

  • Received: August 03, 2009

Recommend & Share

  • Share on ACS NetworkACS Network
  • Add to FacebookFacebook
  • Tweet ThisTweet This
  • Add to CiteULikeCiteULike
  • Add to NewsvineNewsvine
  • Digg ThisDigg This
  • Add to DeliciousDelicious

Related Content