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Mannich Reactions in Room Temperature Ionic Liquids (RTILs): An Advanced Undergraduate Project of Green Chemistry and Structural Elucidation
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Abstract
This is a mini laboratory project on green chemistry suitable for junior-level students. The objective of this experiment is to allow students to gain exposure to the innovative ideas of current chemistry research and experience research-oriented work as in postgraduate studies. Recent research has shown that room temperature ionic liquids (RTILs) are promising replacements for traditional volatile organic solvents for organic reactions. RTILs, being ionic compounds, have the advantages of low volatility, good chemical and thermal stabilities, good activity for a variety of organic reactions, and are readily recyclable so that chemical waste disposal can be minimized. This experiment describes the synthesis of a commonly used ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate, [bmim][BF4], and the application of this ionic liquid as a recyclable medium for Mannich reactions. Benzaldehyde, 3-pentanone, and ammonium acetate undergo a stereospecific double Mannich reaction when mixed in the ratio of 2:1:1 in [bmim][BF4] and give a tetrasubstituted piperidone as the product. Students are required to identify the chemical structure and the stereochemistry of the product by examining the mechanism of the reaction and the spectroscopic data.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Feature):
Green ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
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- Received: August 03, 2009
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