ps7 - electrophilic substitution on a disubstituted benzene...

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Massachusetts Institute of Technology 5.12 Spring 2005 Problem Set 7 Due April 21 4pm 1. Propose a synthesis. OH 1
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2. Provide the major products. (CH 3 ) 3 CCH 2 Cl, AlCl 3 3. Toluene is ortho, para directing while trifluoromethylbenzene is meta directing. Explain, using resonance structures in your answer. vs. 3 CF 2
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4. List the following compounds in order of acidity. (1 = most acidic) OH OH OH MeO OHC Cl 5. List the following compounds in order of basicity. (1 = most basic) NH 2 NH 2 NH 2 Me Br O 2 N 3
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6. Propose a mechanism. H + 4
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7. Outline a multistep synthesis of 1-ethyl-4-nitrobenzene from toluene. 3 2 D CH CH NO 2 5
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8.a-c Which of the following compounds can likely be prepared in a pure state by
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Unformatted text preview: electrophilic substitution on a disubstituted benzene? Outline the method in each case. a OCH 3 NO 2 NO 2 b COOH NO 2 COOH c NO 2 NO 2 O 2 N 6 8.d-f Which of the following compounds can likely be prepared in a pure state by electrophilic substitution on a disubstituted benzene? Outline the method in each case. d NO 2 NO 2 NO 2 OH Br e Br f NO 2 Br COOH 7 9. Provide a detailed stepwise mechanism for the following reaction. Cl OMe 2 -NO MeO NO 2 Cl-NO 2 NO 2 8 10. Propose the mechanism of the following reaction and provide the MAJOR product. H 2 SO 4 /HNO 3 9...
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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ps7 - electrophilic substitution on a disubstituted benzene...

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