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HT3-05 - Hour Examination#3 Chemistry 302-302A Chemiftry is...

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Hour Examination #3, Chemistry 302-302A, April 28, 2005 “Chemiftry is the art of decompounding bodies .... Thomas Southwell, M.D. London, 1764. 1 (20 points). Alcohols, R-OH, are generally converted into halides, R-X, on reaction with HX. Thus: OH HCl Cl (a) Write a mechanism for this change. (b) Professor Les Gometz, ever the generalist, expected that optically active alcohol 1 would follow a similar path. Also, being very sophisticated mechanistically, Les was confident that the stereochemistry of the product 2 would be as shown, and that 2 would still be optically active. Br OH HCl Br Cl 1 (optically active) 2 (optically active) Imagine his surprise when the product turned out to be racemic 2a . Explain mechanistically. Br OH HCl Br Cl 1 (optically active) 2a (racemic) 2 (15 points). Provide a mechanism for the Schmidt reaction, shown below. Please note - the reagent really is hydrazoic acid, HN 3 , not ammonia NH 3 . R OH C O H—N 3 H 2 O R—NH 2 N 2 CO 2 + +
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3 (15 points). The characteristic brown color of toast (and roast chicken) is the result of the Amadori reaction shown below. Provide a mechanism for this transformation:
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