Friday_Session_3___Solution - Chem 3580 - Spring 2009...

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Chem 358 0 - Spring 2009 Friday Session #3 – Feb 05 2009 - Solution 1. Br NO 2 Br NO 2 Br NO 2 Br NO 2 NO 2 Br NO 2 NO 2 > > > > 2. Cl Cl O 2 N NO 2 NaOCH 3 CH 3 OH Cl CH 3 O O 2 N NO 2 3. Synthesis (a) CH 3 Excess H 2 SO 4 , ! CH 3 O 2 N NO 2 CH 3 H 2 N NH 2 CH 3 HO OH NO 2 NaNO 2 , HCl CH 3 HO OH CH 3 N 2 N 2 Cl H 2 , Pd/C CH 3 Br AlCl 3 HNO 3 Cu 2 O Cu(NO 3 ) 2 Cl 0°C Could make TNT, a dangerous explosive, since toluene is an activated ring HNO 3 CH 3 COOH Low Temp Very highly activated and will be difficult to control the reaction Br H 2 SO 4 , ! Br O 2 N NO 2 Br H 2 N NH 2 Br HO OH NO 2 Br HO OH Br N 2 N 2 Cl H 2 , Pd/C HNO 3 Cu 2 O Cu(NO 3 ) 2 Cl CH 3 HO OH NO 2 Br 2 FeBr 3 NaNO 2 , HCl 0°C (CH 3 ) 2 CuLi Alternative that avoids some of the shortfalls, especially the potentially explosive reactions. A deactivated ring HNO 3 CH 3 COOH Low Temp Less activated ring than in the first method
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(b) CHO O 2 N NH 2 CH 3 Excess 1. NBS, peroxide 2. HO 3. PCC or MnO 2 CHO HNO 3 H 2
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Friday_Session_3___Solution - Chem 3580 - Spring 2009...

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