The Dehydration of Cyclohexanol

The dehydration of cyclohexanol, specifically by way of semi-microscale is the product from an E1 reaction that also results in two isomeric alkenes emerging by virtue of Zaitsev’s rule that favors the most stable/ alkene meaning more alkyl groups bonded to the carbons. During the experiment color change was witnessed while heating to get a distillate that would eventually separate into two layers. The layer on top would eventually be dried with anhydrous Calcium Chloride and liquid collected from layer. Testing the product with Ammonium Cerium (IV) Nitrate, Bromine, and Refractive Index to verify the compound we have is cyclohexene. For Ammonium Cerium (IV) Nitrate and Bromine test, color was the main indicator. With the refractive index, the value of 1.4462 at 22°C came close to literature values of 1.4460 at 20°C. During the heating of hexanol some concern was brought up by the position of the condenser. The position was closer to a parallel orientation instead of having a sloped pitch toward the collection vessel. There were large drops accumulating toward the thermometer side of the condenser but leveling the condenser in a way to increase pitch solved the problem. Increasing pitch may have led to a greater amount of distillate. Additionally, throughout the experiment there were many vapors that led so mild headaches between group members, regardless of working in the hood or not. When recreating the experiment, more precaution should be used to contain chemicals under the fume hood. There are large implications to the use of dehydration reactions, especially in biological aspects. For instance, dehydration of two glucose monomers to produce a a disaccharide maltose along with water is just one of many reactions that use dehydration synthesis, the creation of a single compound by removing water.

Refrences

Signature Lab Series. (2004). Mason, OH: Cenage Learning Experiment 712; Dehydrating Cyclohexanol. Wigal, T. Carl. Lebanon Valley College