Problem_Set_11

Problem_Set_11 - hydroxide) compound B was obtained, which...

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Chem 358 Spring 2007 Problem Set 11 Chapter 23 : 23 .38a, c, e-h, 39a, b, c, e, g, 40a, b, f, g, i, k, j, 41a, d, 46, 47, 49, 50, 55, 59, 60g-o, 61, 68, 69, 71 The following problems will be worked out during Friday’s problem working session. Solutions will be posted. 1. Provide a mechanism for the reaction shown below. Provide a reason for why the reaction goes in the direction of the arrow and why one full equivalent of base is used. Claisen reaction is reversible. OEt O O 1. EtO 2. H + OEt O O OEt O 2 1 2. Propose a plausible mechanism for the reaction shown below. Draw all important resonance structures for intermediates. O O O O O O NaOEt EtOH 3. When compound A was heated with sodium hypobromide (NaOBr or Br 2 in sodium
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Unformatted text preview: hydroxide) compound B was obtained, which in turn was converted into C by heating. Mechanistically account for these results. NH 2 H 2 N O O HO O NH 2 N O H Br 2 , NaOH ! A B C 4. Show the following compound might be synthesized by a combination of Mannich reaction and Hofmann elimination. O O 5. Propose a practical laboratory synthesis of the compounds shown below from the indicated starting compounds. Use any necessary inorganic reagents and, where appropriate, use any other organic reagents containing no more than 4 carbon atoms. More than one step is needed in each case. EtO OEt O O OH O MeO O O O O H O O CCOH OH CF 3 and O CF 3 PROZAC N CH 3 H CH 3 CH 3 HO OH NH 2...
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This note was uploaded on 04/22/2009 for the course CHEM 3570 taught by Professor Ganem, b during the Fall '06 term at Cornell.

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Problem_Set_11 - hydroxide) compound B was obtained, which...

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