Oxidation of Cyclododecanol to Cyclododecanone

The objective of this lab was to create a ketone through an oxidation reaction using a using a secondary alcohol and oxidizing agent in order to use that ketone in a reduction reaction with a specific reducing agent to determine the affect of that reducing agent on the diastereoselectivity of the product. In the first part of this experiment, 4-tert-butylcyclohexanol was reacted with NaOCl, an oxidizing agent, and acetic acid to form 4-tert-butylcyclohexanone. In the second part of this experiment, 4-tert-butylcyclohexanone was reacted with a reducing agent, either NaBH4 in EtOH or Al(OiPr)3 in iPrOH, to form the product 4-tert-butylcyclohexanol. 1H NMR spectroscopy was used to determine the cis:trans ratio of the OH relative to the tert-butyl group in the product formed from the reduction reaction with each reducing agent. Thin-layer chromatography was used in both the oxidation and reduction steps to ensure that each reaction ran to completion.

Beran, J. A. Laboratory Manual for Principles of General Chemistry. 9th ed. Hoboken, NJ: John Wiley; 2010

The products of the primary alcohol reaction, 1-butanol and HCl, are 1-chlorobutane and water; products of the secondary alcohol, 2-butanol and HCl are 2-chlorobutane and water; products of the tertiary alcohol, 2-methyl-2-propanol are 2-methyl-2-chloropropane and water.

The Purpose of this experiment is for the students to learn how to use sodium borohydride to reduce benzil to its secondary alcohol product via reduction reaction. This two-step reaction reduces aldehydes by hydrides to primary alcohols, and ketones to secondary alcohols. In order for the reaction to occur and to better control the stereochemistry and yield of the product, the metal hydride nucleophile of the reducing agents such as LiH, LiAlH4, or NaBH4 must be carefully chosen. Being that LiAlH4 and NaBH4 will not react with isolated carbon-carbon double bonds nor the double bonds from aromatic rings; the chosen compound can be reduce selectively when the nucleophile only react with

In the Cannizaro reaction an aldehyde is simultaneously reduced into its primary alcohol form and also oxidized into it 's carboxylic acid form. The purpose of this experiment is to isolate, purify and identify compounds 1 and 2 which contain 4-chlorobenzaldehyde, methanol, and aqueous potassium hydroxide. Compounds 1 and 2 are purified by crystallization. . The purified product will be characterized by IR spectroscopy and melting point.

Mayo, D. W.; Pike, R. M.; Forbes, D. C. Microscale Organic Laboratory with Multistep and Multiscale Syntheses, 5th ed.; John Wiley & Sons, Inc., 2011; pp 132-135.

Purpose: The purpose of this experiment is to observe a variety of chemical reactions and to identify patterns in the conversion of reactants into products.

The melting point of the final product, diphenylacetylene, was found to be 65-68 degrees Celsius which is right around the ideal 61 degrees Celsius melting point; this shows that purification during the lab worked and that the sample was almost 100% pure. Since only 0.01g of diphenylacetylene was collected and the theoretical yield was calculated to be 0.049g, this experiment had a 20.41% yield. A few sources of error that explain the low percentage could be the loss of crystals when transferred from the test tube to the suction apparatus or when they were transferred from the suction apparatus to the filter paper to be dried and then weighed. Crystals could have also been lost if more than 5 drops of methanol was added because excess methanol would dissolve the crystals. The experiment was successful when looking at the crystals collected from the addition step and the elimination step; however, to improve the percent yield and collected product the the test tubes could have been allowed to cool down in the ice bath past the 5 minutes to ensure all the crystals formed

2. Plan: Each student in a group of three will work to create a reaction with the Benzonitrile Oxide with, cis-stilbene, trans-stilbene, or styrene in an Erlenmyer flask. With this Reaction solution thin layer chromatography will be performed using each reaction solution. The different reactions will then be compared by running co-spot TLC’s. An NMR of the crude products from each reaction will be taken.

In this experiment, the main objective was to synthesize a ketone from borneol via an oxidation reaction and secondly, to produce a secondary alcohol from camphor via a reduction reaction. Therefore, the hypothesis of this lab is that camphor will be produced in the oxidation reaction and isoborneol will be the product of the reduction reaction because of steric hindrance. For the oxidation step, a reflux will be done and then a microscale reflux for the reduction step. The products will be confirmed using Infrared spectroscopy, the chromic acid test, 2,4-DNP test and 13C NMR spectroscopy. The results of this

Dictionary of organic compounds, 6th edition, Chapman and Hall, London, Volume 3(& Volume 6), 1996 Maria Lindsay and Sean P. Hickey, Organic chemistry lab 2 manual, department of Chemistry University of New Orleans

Fifield, F. W. and Kealey, D. 1995. Principles and Practice of Analytical chemistry. (4th ed) Glasgow, Blackie Academic and professional.

Timberlake, K. C. (01/2014). Chemistry: An Introduction to General, Organic, and Biological Chemistry, 12th Edition.

The main production process for cyclopentanol was cyclopentanone hydro-conversion, and the cyclopentanone was produced by decarboxylation of adipic acid at high temperature. (Yao et al., 2014)

Hellwinkel, D. (1998). Die systematische Nomenklatur der Organischen Chemie (4th ed.). Berlin: Springer. p. 45. ISBN 3-540-63221-2.