University:
Purdue University
Course:
CHM 34201 | Inorganic Chemistry Laboratory
Academic year:

2023
Views:

450

Pages:

4
Author:

Leilani Contreras

Oxidation of Cyclododecanol Introduction: The purpose of this lab was to oxidize Cyclododecanol to form Cyclododecanone by using dehydration to remove a functional group off of Cyclododecanol and replace it with a ketone to form Cyclododecanone. Theory: The reaction taking place is a redox reaction, where one species is oxidized and one is reduced. The species that is oxidized loses electrons and the species that is reduced gains electrons. Redox reactions tend to mean the loss or gain of electrons, but in Organic Chemistry it refers to the addition or reduction of an Oxygen bond. In our reaction, NaClO is the oxidizing agent and Cyclododecanol is being reduced. When this happens, we can see this change in the Fourier-transform infrared spectroscopy (FTIR), which shows us what functional groups there are in a compound. Procedure: Setup: -Combine .5g cyclododecanol, 1.2mL acetone, and .4mL of glacial acetic acid in a 25mL round bottom flask. Add a stir bar and position the flask inside a cloth heating mantle above a stir plate. Attach the water hoses and secure all parts in place with clamps. Oxidation: -Heat mixture to reflux and add 15mL of bleach dropwise over 15min. Allow mixture to reflux for 15min. then cool solution. Test the solution with iodine test paper. Workup: -When the mixture is cooled, transfer into a separatory funnel and shake the two-phase mixture and separate into organic A and aqueous B. Remove aqueous layer and further extract extra aqueous layers. -Filter through a funnel with flter paper and remove the solvent by rotary evaporation. Recrystallization: -Recrystallize the crude cyclododecanone with a mixture of methanol and water. Obtain a melting point of the final product. IR Spectroscopy: -Obtain a salt plate and place a small spatula tip of your product in a test tube. Dissolve in .5mL dichloromethane and place a couple drops on the salt plate and blow till white film forms. Results: Started with .5g of cyclododecanol, melting point 76-79 Finished with .41g of cyclododecanone, recovered 82%, melting point 59-62, experimental melting point 56 Starting out the experiment with .5g of cyclododecanol and finishing with .41g of cyclododecanone gives us a 82% recovery. There could be potential human error which resulted in a lower %recovery. The experimental melting point was only 3 degrees off of the actual melting point, but there were still impurities in our final product. Our FT-IR gave us peaks at 1700 and 2800 and this was expected because of the double bonded Oxygen and single bonded Carbon Conclusion: The results of this experiment seemed to be successful, with only some minor impurities in our sample, it gave us near perfect results. There were no real surprises in the results and it was a very successful experiment.