Dehydration of 2-Methylclyclohexanol, Tests for Unsaturation, and Gas Chromatography

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Ashley Peccatiello Experiment 7 – Dehydration of 2-Methylclyclohexanol, Tests for Unsaturation, and Gas Chromatography Date Performed: October 25, 2012 Date Written: October 29, 2012 Purpose: To dehydrate 2-methylclyclohexanol to obtain two isomers. To separate the products by simple distillation. To analyze the sample by introducing the technique of gas chromatography and unsaturation tests. Reaction: Figure 1. Overall reaction of the acid-catalyzed dehydration of 2-methylcyclohexanol Figure 2. Reactions for the unsaturation tests Table of Reactants and Products: Table 1. Molecular weight, density, melting point, and boiling point for all reagents used in Experiment #7 – Dehydration of 2-Methylclyclohexanol, Tests for Unsaturation, and Gas Chromatography. Name: | MW (g/mol): | Density (g/mL): | MP (C): | BP (C): | MSDS: | 2-methylcyclohexanol | 114.19 | 0.93 | -38.00 | 165-168 | Irritant, flammable | 95% phosphoric acid | 97.994 | 1.69 | 42.35 | 158 | Corrosive, irritant | 1-methylcyclohexene | 96.17 | 0.81 | -120.4 | 110 | Irritant, flammable | 3-methylcyclohexene | 96.17 | 0.81 | -124.00 | 104 | Irritant, flammable | Procedure: Part One – Dehydration of 2-methylcyclohexanol A microdistillation apparatus was assembled by securing a microdistillation flask to a ring stand and submerging it in an empty heating mantle. A thermometer and Teflon adaptor were tightly sealed into the top of the flask with the thermometer bulb being below the side arm. The collection flask was secured at the end of the side arm. Sand was added to the heating mantel until the flask bulb was mostly covered. The heating mantel was connected to a variac prior to the outlet. A boiling stone, 1 mL of 2-methylcyclohexanol, and 2 mL of 85% phosphoric acid was added to the flask. The sample was heated gently, keeping the temperature below 96C, until .5 mL of

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