Oxidation of Cyclododecanol to Cyclododecanone

The sodium hydroxide acts to pull the hydrogen off the oxygen in the 2-methylphenol so that the oxygen has a negative charge and can attack the sodium chloroacetate. Again, using a 1:1 molar ratio, 0.34 g (2.9 mmol) of sodium chloroacetate (the good leaving group) was added to 1 ml of water and dissolved. Following dissolving all of the 2-methylphenol (to avoid the sodium hydroxide reacting concurrently with the sodium chloroacetate and 2-methylphenol) in the sodium hydroxide, the aqueous solution of sodium chloroacetate was transferred to the reaction flask. This mixture was then heated to reflux, using a medicine dropper affixed to the top of the flask as an alternative method to boil without

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.

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

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

6. Purpose: to clarify the mechanism for the cycloaddition reaction between benzonitrile oxide and an alkene, and to test the regiochemistry of the reaction between benzonitrile oxide and styrene; to purify the crude product of either trans-stilbene, cis-stilbene, or styrene reaction.

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.

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

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

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.

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

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

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

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 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.