Problem_Set_10 - O O 3. Write down the major organic...

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Chem 3580- Spring 2009 Problem Set 10 Chapter 20 : 27-33, 35, 39, 41-46, 48, 49 [I suggest you also go to Friday session #6 and do questions 2 (synthesis) and 3 (amine reaction mechanisms). The solutions to these have been posted.] 1. When compound A was heated with sodium hypobromide (NaOBr or Br 2 in sodium 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 2. Show how the following compound might be synthesized by a combination of Mannich reaction and Hofmann elimination.
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Unformatted text preview: O O 3. Write down the major organic product(s) of each of the following reactions. N 1. CH 3 I (excess) 2. Ag 2 O, H 2 O 3. ! (a) NH O O 1. KOH 3. NaOH, H 2 O, ! O 2. (b) NMe 3 HO — (c) ! Ph H CH 3 H 3 C H N 1. H 2 O 2 2. ! (d) 4. Propose a practical laboratory synthesis of the compounds shown below from the indicated starting compounds. Use any necessary inorganic reagents and any other organic reagents. More than one step is needed in each case. O OH NH 2 ? ? NH 2 NH 2 OH O N H OH O NH 2 OH O N O O H (a) (b) (c) (d) (e) (f) ? ? ? ?...
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell University (Engineering School).

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Problem_Set_10 - O O 3. Write down the major organic...

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