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CHEM 222
David Harpp

Chemistry 222 Fall 2012 Experiment 1: Oxidation of an Alcohol – Report Sheet Last Name: Siva First Name: Krishnaa Date: October 11, 2012 Section Number: Chem 222-05 Objective: 1 mark (What is the purpose of this experiment?) The objective of this experiment is to oxidize cyclohexanol, a secondary alcohol, by reacting it with sodium hypochlorite and form cyclohexanone, a ketone. The reaction is performed with the help of acetic acid which activates it. At the end of the lab, with the use of IR spectroscopy, the product is to be verified if it is actually cyclohexanone. Introduction: 2 marks (Brief description of the concept/reaction studied – oxidation of an alcohol) The oxidation of an alcohol to an aldehyde, ketone, or carboxylic acid plays a huge role in organic chemistry. Primary alcohols can be oxidized into aldehydes and then further oxidized to carboxylic acids, while secondary alcohols can be oxidized into ketones. It is important to note that the oxidation process normally consists of two reactions. The first part of the reaction consists of the nucleophilic addition and the second part consists of the E2 elimination. In this lab, cyclohexanol, a secondary alcohol, reacts with bleach (sodium hypochlorite) to form cyclohexanone, sodium chloride and water. Acetic acid is used in this experiment to activate the sodium hypochlorite and allow the reaction to proceed. While performing the lab, it is important to be safe and careful. For this reason being, beach is chosen as the oxidizing reagent over any other oxidant. Sodium hypochlorite is easier to control compared to many other oxidizing agents and it is environmentally friendly. Reaction Equation: 2 marks (Include proper structures and data [molar mass, concentration, density, volume, mass, moles, etc – as appropriate – including theoretical yield] for reactants and products) 1 Chemistry 222 Fall 2012 Molar Melting mass Point Boiling Density (g/mol) (̊ ) Point ( ̊C)(g·cm−3) Volume/Mass Moles Sodium Hypochlorite 74.440 18.0 101.0 1.110 36 mL 0.537 Acetic Acid (catalyst) 60.050 16.0 18.0 1.050 1.2 mL 0.021 Cyclohexanol 100.158 25.9 160.8 0.962 2.4 mL 0.023 Theoretical: Theoretical: 2.267 g 0.0231 Experimental: Experimental: Cyclohexanone 98.150 -16.4 155.6 0.947 1.45 g 0.0148 Sodium 1413.00 Chloride 58.440 801.000 0 2.160 4.0 g 0.068 Water 18.015 0.000 99.980 1.000 - - Table 1. Results – Yield and Physical Properties of Cyclohexanone 5 marks Cyclohexanone Yield (g) 1.45 g Yield (%) 64 % Appearance Colorless liquid (clear), thick looking -1 IR (C=O stretch at ~1715 cm (corresponds to the graph, long stretch) evident stretch can be seen) Figure 1. IR Spectrum Attach IR Spectrum of Your Cyclohexanone Product – label important stretching frequencies Discussion Questions: 10 marks 1.Suggest at least one chemical reasons why your percent yield is less than 100%. (Incomplete reactions? Side reactions? Stability of reagents?) One possible reason why the percent yield is less than the expected yield is due to the improper pace at which the sodium 2 Chemistry 222 Fall 2012 chlorite is added. The rapid addition of the bleach (sodium hypochlorite) to the reaction flask with the acetic acid and cyclohexanol would cause the reaction to take place vigorously, and would result in an incomplete reaction. Unclean materials and instruments could have affected the yield of the experiment as well. The presence of chemicals used in the previous experiments will certai
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