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Chemistry 30A3 Fall 2011 Labs Dr. Troendle 51

Chemistry 30A3 Fall 2011 Labs Dr. Troendle 51 - is 286-295...

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Chemical Biology 3OA3, September 2009 Page 51 Dilantin In a 25 mL round-bottomed flask equipped with a stirring bar place 400 mg of unrecrystallized benzil, 200 mg of urea, 6.0 mL of ethanol, and 1.2 mL of 30% aqueous sodium hydroxide. Attach an upright condenser (to avoid "freezing" the ground glass joint use a dab of stopcock grease), and boil the brownish mixture gently for 1 h with stirring. Cool the reaction mixture, add 10 mL of water and if a ppt is present, filter the solution to remove a sparingly soluble side product that sometimes forms. Acidify the clear brownish filtrate with dilute hydrochloric acid, collect the product on a suction filter, and wash it thoroughly with water. The product may be recrystallized from ethanol. The yield is 0.28-0.40 g. The recorded melting point
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Unformatted text preview: is 286-295 ° C; do not attempt to determine the melting point with an oil bath. Collect an IR spectrum. (Caution-Dilantin is a powerful therapeutic agent and must be taken only on the advice and supervision of a physician!) Questions 1. Draw the structure of the product formed by addition of vitamin B 1 and benzaldehyde. 2. Ammonia adds to carbonyl groups but it is ineffective as a catalyst for the benzoin condensation. Explain. 3. Devise a very simple method for studying the kinetics of the oxidation reaction. 4. Write a detailed step-by-step mechanism for the reaction of benzil with urea in the presence of hydroxide ion. 5. In dilantin sodium, it is the imide proton that is abstracted rather than the amide proton. Why?...
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