CHED 392 |
| The dehydration of alcohols to form alkenes is one of the fundamental laboratory operations performed by students enrolled in introductory organic chemistry. Traditionally, these processes have been promoted by a variety acids, including concentrated sulfuric and 85% phosphoric acid. Recent disclosures reveal that acidic resins can function as dehydrating agents in several types of dehydration processes, including Fischer esterifications and alcohol elimination reactions. We have investigated the scope of the acidic resin catalyzed dehydration of a variety of alcohols [1-methyl-1-cylcohexanol (3o); cyclohexanol (2o); 4-methyl-2-pentanol (2o); and 4-methyl-1-pentanol (1o)] utilizing a variety of acidic resins [Dowex 50WX2-100, Amberlite IRC-50S, and Amberlysts 15, 15(wet), and 36(wet)]. These studies culminated in the development of microscale alcohol dehydration procedures that produce either one alkene (from cyclohexanol), two alkenes (from 1-methyl-1-cyclohexanol), or a mixture of alkenes from substrates that undergo carbocation rearrangements (the pentanols). Product identities and yields were determined by GCMS and standardized GC. |
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Undergraduate Research Poster Session: Chemical Education
11:00 AM-1:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Chemical Education |