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  Home > JCE Print > Journal of Chemical Education > Issues > 2007  > March  >
In the Laboratory
Green Chemistry
The Aldol Addition and Condensation: The Effect of Conditions on Reaction Pathway
R. David Crouch, Amie Richardson, Jessica L. Howard, Rebecca L. Harker, and Kathryn H. Barker
Department of Chemistry, Dickinson College, Carlisle, PA 17013-2896
Cover
March 2007
Vol. 84 No. 3
p. 475

Abstract
The reaction of a ketone and an aldehyde in aqueous Na2CO2 is described. This experiment is performed in the absence of strong bases or organic solvents and offers the opportunity for students to observe the critical role that reaction temperature and base strength have in determining the product of the base-mediated addition of a ketone to an aldehyde. When the reaction takes place at room temperature, the aldol addition product is produced. But, when the reaction is heated to 50 °C, the aldol condensation product is isolated. Both reactions use the same quantities of reagents. The reaction temperature is the factor that determines which product is formed. When NaOH is used in place of Na2CO2, the aldol condensation product is isolated regardless of temperature.
Supplement
Instructions for the students and notes for the instructor including 1H NMR spectra are available.
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Citation
Crouch, R. David; Richardson, Amie; Howard, Jessica L.; Harker, Rebecca L.; Barker, Kathryn H. J. Chem. Educ. 2007 84 475.
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Keywords
Addition Reactions; Aldehydes / Ketones; Green Chemistry; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Reactions; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
2/1/2007
2/16/2007
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Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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