The Effect Of Acid Catalyzed Elimination Of Water From Cyclohexanol

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.

Abstract: Using hypochlorous acid to convert secondary alcohol called cyclododecanol to the corresponding ketone which is cyclododecanone by oxidation.

Working in the hood or a designated work area, add about 1 mL of ethyl alcohol to a clean evaporating dish. Place the evaporating dish on a heat- resistant pad.

The crude product was washed by taking the reaction product in the separatory funnel and adding 23 mL of deionized H2O. The mixture was shaken and allowed to settle until layers were observable. The top layer was the desired product and approximately 25 mL of aqueous layer was extracted from the separatory funnel. Next, 25 mL of 5% NaHCO3 was added to the separatory funnel in order to neutralize the acid. This mixture was swirled, plugged with the stopper and inverted. Built-up gas was released by turning the stopcock to its opened and closed positions, releasing CO2 by-product. This was done four times in one minute intervals. The solution was allowed to settle until layers were observable. The bottom layer that contained salt, base and water was extracted from the separatory funnel. The crude product was washed again as mentioned previously.

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.

8.When the reaction is completed, record the volume of gas in the graduated cylinder. Record observations about which reactant was the limiting reactant.

The purpose of this lab was to carry out a dehydration reaction of 2-methylcyclohexanol by heating it in the presence of phosphoric acid and determining which alkene product would be the major product. Methylcyclohexanols were dehydrated in an 85% phosphoric acid mixture to yield the minor and major alkene product by elimination reaction, specifically E1. The alkenes were distilled to separate the major and minor products and gas chromatography was used to analyze the results and accuracy of the experiment. The hypothesis was the major product of the reaction would be the most substituted product. This conclusion was made because of

alcohol (2-methyl-2-butanol, MW _ 88.2, d _ 0.805 g/mL) and 25 mL of concentrated hydrochloric acid (d _ 1.18 g/mL). Do not stopper the funnel. Gently swirl the mixture in the separatory funnel for about 1 minute. After this period of swirling, stopper the separatory funnel and carefully invert it. Without shaking the separatory funnel, immediately open

Aim The purpose of this experiment was to convert a cyclohexanol to a cyclohexene through E2 reaction by dehydration. Introduction

6 cylinders of the same size by using a cork. I got six beakers and filled each with 20 mL of the

Add 30 ml of DI water into beaker then stir with glass rod, the beaker can now be removed from the fume hood

An E1 (unimolecular elimination) reaction is an organic reaction where two groups are removed from the starting molecule in a two-step mechanism. The first group that leaves forms a carbocation intermediate, and the second group that leaves causes the formation of a double bond1. The formation of the carbocation ion in the intermediate is important because that determines the rate of the reaction. If a more stable carbocation can be formed, shifts may occur because the more stable the carbocation intermediate, the faster the reaction can go. Often, two products can result from an E1 reaction; however, it is possible that there is more yield of one product over the other. What makes a product major or minor can be understood with Zaitsev’s rule which states that the product with the most substituted double bond is more stable and will therefore be the major product2. The specific E1 reaction observed in this lab is the acid catalyzed dehydration of 2-methylcyclohexanol. In this case, the first group to leave is an H2O molecule, and the second group to leave is a H+. Two products will result from this reaction- 1-methylcyclohexene and 3-methylcyclohexene. Below in Figure 1 shows the two- step mechanism that occurs.

Cyclohexanol, the reagent of this experiment, is used in the production of nylon, paints, plastics, detergents, textiles and pesticides. The dehydration of cyclohexanol to cyclohexene can be accomplished by pyrolysis of the cyclic secondary alcohol with an acid catalyst at a moderate temperature or by distillation over

· Measure out 10ml of acid and add it to the conical flask and start

The materials you will need are forceps, a pencil, yeast solution, hydrogen peroxide, filter paper disks, six 250 ml beakers, distilled water, paper towels, and graph paper. These concentrations below will be put into each beaker. Be sure to label each beaker.