Cyclohexanone Oxime Synthesis Lab Report

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Title: Cyclohexanone Oxime Synthesized from Cyclohexanol Name: Keegan Rayford Date: Thursday 1:15, February 26, 2012 Introduction: The synthesis of cyclohexanone oxime is used was done in two steps. First, cyclohexanol was oxidized into cyclohexanone. This was accomplished by adding bleach and the oxidizing agent glacial acetic acid to cyclohexanol. Oxidizing is the addition of oxygen to a compound and the loss of hydrogen resulting in a C=O bonds. In this specific reaction a ketone was formed from the oxidation of cyclohexanol. Infrared spectroscopy was then used to analyze the product to determine if the alcohol was removed. Next, cyclohexanone oxime was formed from the cyclohexanone created in the previous lab. Cyclohexanone oxime is important in the synthesis of Nylon-6, one of the most used nylons in the world, because it rearranges to the starting material of Nylon-6. Nylon-6 is commercially used to make shoe laces and car tire tread. Oximes have also shown that they as drugs can possibly reduce the impact of organophosphate poisoning. The final product was then analyzed by melting point to test purity. Chemical Reaction: Data and Observation: Oxidation of Cyclohexanol * 0.98 ml of Acetic Acid * 2.18 ml of Cyclohexanol * 29.8 ml of Bleach * 0.811g of Sodium Thiosulfate * 1.898g of Sodium Bicarbonate * 5.028g NaCl * When acetic acid, cyclohexanol, and bleach where all added into the flask a cloudy, yellow liquid formed. * First starch paper turned black. * Second starch paper stayed white. * First pH turned red. * Second pH paper stayed blue. * When NaCl was added, a cloudy, white liquid bottom liquid formed and a thin clear liquid layer formed. * Preweighed cap + vial = 4.787g * Cap + vial + liquid =5.629g * Grams of Cyclohexanone recovered = 0.842g * Theoretical Maximum of Cyclohexanol =
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