Contact Information

Author
  • Robert D. Singer
  • Professor
  • Chemistry
  • Saint Mary's Univ.
  • Halifax, Nova Scotia, Canada
  • B3H 3C3
Email
Phone
(902) 496 - 8189
Website

Cocrystal Controlled Solid-State Synthesis: A Green Chemistry Experiment for Undergraduate Organic Chemistry

Author Contact: robert.singer@smu.ca

Summary

In this set of experiments students will be introduced to condensation reactions, green chemistry and cocrystal controlled solid state synthesis. This type of solid state synthesis is performed by first making cocrystals of the two reactants (in this case an anhydride and an amine) which brings the reactive functional groups in close proximity to one another, allowing for a reaction to occur when heated.

A very interesting aspect of this lab is that students can perform the reaction under a variety of conditions including solvent-free or with microliter amounts of methanol of DMF. A possible project could be to have students form groups and perform the reaction under different conditions and then compare the different methods using a variety of metrics such as yield, atom economy, E-factor, and hazards.

Supplemental information includes detailed background information, experimental procedures, safety and hazards, instructor notes, materials list, color pictures of reagents, intermediate and product and spectrographic data.

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

Source

Cheney, M. L.; Zaworotko, M. J.; Beaton, S.; Singer, R. D. J. Chem. Educ., Print 2008, 85, pp 1649-1651.

J. Chem. Educ. (Abstract only)

Category Descriptors

Chemistry Concepts
  • Amines-Ammonium Compounds
  • Carbonyl Chemistry
  • Crystal Engineering
  • Heterocycles
  • Solid State Chemistry
Laboratory Techniques
  • Calorimetry/Thermochemistry
  • Heating and Cooling Methods
  • IR Spectroscopy
  • Melting Points and Melting Ranges
  • Microscale Lab
  • NMR Spectroscopy
  • Recrystallization
  • Vacuum Filtration
Green Chemistry Principles
  • Avoid Chemical Derivatives
  • Maximize Atom Economy
  • Prevent Waste
  • Use Safer Solvents/Reaction Conditions
Chemistry Subdiscipline
  • Organic Chemistry
Target Audience
  • Colleges/Universities
Source
  • Journal Articles