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0320Midterm2 - O AlCl 3 O O O 1 2 O Cl O AlCl 3 O O 3 4 O O...

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1 Chemistry 0320 Midterm Examination 2 October 24, 2008 Name: _____________________________ 1. Functional definitions. Provide structures that fit the following descriptions. (15 points) (a) A diazonium ion. (b) A phosphonium salt. (c) An activating group for nucleophilic aromatic substitution. (d) A compound that can undergo a Claisen rearrangement. (e) An ether that can be cleaved by hydrogenolysis.
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2 2. Theory. a) Trifluoromethyl ketones are much more likely to exist as hydrates than methyl ketones. Explain this observation. (10 points) CF 3 O + H 2 O CF 3 HO OH CH 3 O + H 2 O CH 3 HO OH
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3 b) Bromination of propylbenzene under free radical conditions provides the benzylic bromide as the exclusive product. (10 points) NBS light Br
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4 c) Ester 1 provides para -isomer 2 as the major product upon reaction with acetyl chloride and AlCl 3 , while ester 3 provides meta -isomer 4 under the same reaction conditions. Explain this difference in regioselectivity. (10 points) O O + Cl
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Unformatted text preview: O AlCl 3 O O O 1 2 O + Cl O AlCl 3 O O 3 4 O O 5 4. Reaction recognition. Provide plausible identities for the unknown entities in the reactions shown below. Include stereochemistry where relevant. If no reaction is expected, simply write NR. Some transformations might require more than one reagent or step. (35 points) (a) NO 2 Cl NaOMe ???? (b) ???? CF 3 CO 3 H O O (c) O ???? MeO OMe 6 (d) MeO Na NH 3 ???? (e) NH 2 ???? C N (f) H O ???? 7 g) O ???? H O 8 5. Synthesis. Propose a synthesis of the following compound from a monosubstituted benzene derivative, any inorganic chemicals, and organic compounds that contain four carbons or fewer. If you can't complete the synthesis with the starting material restrictions, use any starting material you want to get partial credit. (10 points) O 9 6. Mechanism. Write a stepwise mechanism for the following transformation. Use arrows! (10 points) N HCl H 2 O H O + HN...
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