chemlab 9 - Phuong Hoang Chem 3105 541 11/5/08 Experiment...

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Phuong Hoang Chem 3105 – 541 11/5/08 Experiment 9: Dehydration of Cyclohexanol: E1 Elimination I. Purpose: The purpose of this experiment is to perform an E1 elimination reaction, the dehydration of cyclohexanol, and to isolate and characterize the product of this reaction, cyclohenxene. II. Background: The dehydration of 2 o and 3 o alcohols to form alkenes usually follows E1 mechanism. The intermediate carbocations formed are stable; otherwise there will be rearrangements to form stable intermediates. The cyclohexanol used in the experiment forms a symmetrical intermediate, and therefore there will be no rearrangement and can generally form only one C=C. The reaction of cyclohexanol: The role of phosphoric acid in the reaction is to protonate the alcohol group. Since this is a reversible reaction, sulfuric acid will be used to minimize the presence of water. The product will be removed by simple distillation to shift the reaction toward the direction of forming more products, according to Le Chaterlier’s principle. To confirm the presence of the alkene group in the product, a qualitative test using molecular
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This note was uploaded on 01/28/2009 for the course CHEM 3105 taught by Professor Zhang during the Spring '09 term at Texas Tech.

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chemlab 9 - Phuong Hoang Chem 3105 541 11/5/08 Experiment...

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