HT3ans-05 - Answers to Hour Examination #3, Chemistry...

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Answers to Hour Examination #3, Chemistry 302-302A, 2005 1. Part (a) better be easy. ..... OH Cl H Cl OH 2 Cl (b) Odd stereochemical result? Must be a Neighboring Group Problem. What’s the internal nucleophile? Got to be that Br. The rest is easy. Br OH * HCl 1 2a (racemic) Br OH 2 Br achiral - no optical activity possible beyond this point Br Cl Br Cl Br Cl a b from a from b * * = optically active
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2. A mechanism involving an initial acylium ion is also acceptable, but addition - elimination (with OH as leaving group) to give a Curtius - like process is not a good answer. R OH C O H N N 2 R OH C O H OH C OH HN R OH C O H N R OH C O HN R N=N=N N 3 H H—N 3 R—NH 2 R OH C O CO 2 "keto-enol" decarboxylate the carbamic acid
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3. This problem is just an exercise in proton pushing, and doing keto-enol transformations. O CH 2 OH HO HO HO OH H 3 NR H 2 NR O CH 2 OH HO HO HO O H H H 2 NR OH CH 2 OH HO HO HO HO NHR OH CH 2 OH HO HO HO N H R OH CH 2 OH HO HO O NHR OH CH 2 OH HO HO HO O OH CH 2 OH
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This note was uploaded on 10/13/2010 for the course CHEMISTRY V25.0243 taught by Professor Jones during the Spring '10 term at NYU.

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HT3ans-05 - Answers to Hour Examination #3, Chemistry...

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