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The Aldol Addition and Condensation: The Effect of Conditions on Reaction Pathway

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R. David Crouch , Amie Richardson , Jessica L. Howard , Rebecca L. Harker and Kathryn H. Barker

Department of Chemistry, Dickinson College, Carlisle, PA 17013-2896

J. Chem. Educ., 2007, 84 (3), p 475

DOI: 10.1021/ed084p475

Publication Date (Web): March 1, 2007

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

Green Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Addition Reactions

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