Problem_Set_5_Answers - +, H 2 O. COOH COOH NO 2 1. KMnO 4...

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Chem 358 Spring 2007 Problem Set #5 Text Problems Chapter 17 : 17. 10, 11, 12, 13, 14, 17, 18 - See solutions posted for chapter 17 earlier for PS#4 Chapter 18 : 18 .2, 4, 5, 6, 36(c), 38, 39, 40, 42(a), (c), (e), 50, 54(a)-(e), (h), (i), 56(a), (e), (f), (m), 57, 60, 61, 65(a), (b), 66, 68, 70. - Posted – see the web site Additional problems - Answers 1. This is free radical benzylic bromination: H Br Answer: The mechanism: Initiation N Br O O N O O + Br Propagation N O O + H H N O O H H + H N O O Br + H Br N O O + 2. The most reactive ones have NO 2 group ortho or para to the leaving group. So the order is as follows: Br NO 2 Br NO 2 Br NO 2 Br NO 2 NO 2 Br NO 2 NO 2 (Closer; so greater inductive effect) > > > >
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3. Answers. Cl Cl O 2 N NO 2 NaOCH 3 CH 3 OH Cl CH 3 O O 2 N NO 2 Cl ortho or para to NO 2 's is most easily displaced. 1. KMnO 4 , - OH, heat 2. H +, H 2 O COOh COOh HOOC HOOC CH 3 1. (CH 3 ) 2 CHCl, AlCl 3 2. HNO 3 , H 2 SO 4 3. KMnO 4 , - OH, heat 4. H
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Unformatted text preview: +, H 2 O. COOH COOH NO 2 1. KMnO 4 , -OH, heat 2. H +, H 2 O No Reaction (Requires the presence of a benzylic H) 4. There is more than one way of identifying the isoprene units. I have shown the alternative for some of the structures. O O O O 4 4 3 2 1 CH 3 H 3 C H H H 3 C CH 3 !-Cadinene CH 3 H 3 C H H H 3 C CH 3 !-Cadinene CH 3 H 3 C H H H 3 C CH 3 !-Cadinene Note: There was an error in the original structure one extra carbon was inserted between the ring carbonyl group and adjacent quaternary carbon. I apologize for the error. I provided two ways of doing the problem for taxol. H 3 C CH 3 CH 3 HO O O O CH 3 OH O O O H H 3 C O CH 3 O O N O OH O H Taxol H 3 C CH 3 CH 3 HO O O O CH 3 OH O O O H H 3 C O CH 3 O O N O OH O H...
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Problem_Set_5_Answers - +, H 2 O. COOH COOH NO 2 1. KMnO 4...

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