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dehydration of alcohols-col - A Title Dehydration of...

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A. Title: Dehydration of 2-Methylcyclohexanol and Analysis of an Alkene Mixture of GC B. Balanced Chemical Equation: CH 3 CH 2 CCH 3 OHCH 2 CH 3 CH 3 CH 2 CCH 3 CHCH 3 + CH 3 CH 2 CCH 3 CH 2 CH 3 + H 2 O C. Mechanism: Major: CH 3 OH O H 3 + CH 3 OH 2 + CH + CH 3 + O H 2 CH + CH 3 O H 2 CH 3 Minor: CH 3 OH O H 3 + CH 3 OH 2 + CH + CH 3 + O H 2 CH + CH 3 O H 2 CH 3 Least Expected Product:
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CH 3 OH O H 3 + CH 3 OH 2 + CH + CH 3 + O H 2 C + C H - H O H 2 CH 2 D. Table of Reagents: Physical Constants Boiling Point (degrees Celsius) Density (g/mL) 2-Methylcyclohexanol Phosphoric Acid 83 1.685 E. Safety Information: Phosphoric acid is a corrosive liquid that can cause severe burns. Avoid any contact between this acid and your skin or clothing- it is a good idea to wear gloves whenever you are working work concentrated acids. If you come in contact with phosphoric acid, inform your teaching assistant and rinse the area well with cold water. Spills should be cleaned up quickly with a large amount of water. 3-Methyl-3-pentanol, 3-methyl-2-pentene, and 2-ethyl-1-butene are flammable liquids. Do not use any open flames in the laboratory and keep these liquids and their vapors away from the hot plates and hot aluminum blocks. F. Procedure: Place 1.25 mL of 2-Methylcyclohexanol and a magnetic spin vane in a 5 mL conical vial. Place the vial on a stir plate and with the spin vane stirring, slowly add 0.25 mL of 85% phosphoric acid to the vial. After the reagents have thoroughly mixed, attach a Hickman still to the conical vial and place the set up in an aluminum heat block on a hot plate. Attach a water-cooled condenser to the top of the Hickman still. Gently heat the contents of the vial, while stirring, until the solution vaporizes, while maintaining a temperature below 96 degrees Celsius.
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