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PracticeExam3 - Page 1 PRACTICE EXAM Spring 2009 Exam 3 CH...

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Page 1 PRACTICE EXAM Spring 2009 Exam 3 – CH 0320 NAME ___________________________________ Good luck!
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Page 2 1. Give an example for each description. Use Fisher, Haworth, or conformational representations. a) An aldopentose: b) A ketohexose: c) Methyl β -D-ribopyranoside: d) L-xylose: e) Xylitol: f) Any reducing sugar:
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Page 3 2. Provide products for each of the following transformations. H O CHO OH H OH H H HO OH H CH 2 OH H O O H CHO H HO H HO H OH OH H CH 2 OH CHO H HO H HO CH 2 OH CHO H HO H HO CH 2 OH HNO 3 /H 2 O CH 3 NH 2 /H + HS SH BF 3 NHNH 2 HCN Br 2 /H 2 O a b c d e f Mannich 2 equivalents C 7 H 13 NO
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Page 4 3. For each of the following transformations, provide mechanisms. (8 points each) a) Show each bond forming step, including deprotonations and protonations. b) Show correct formal charges on each atom that is not neutral. c) In base catalyzed reactions, show an appropriate source for protonation. (for example, H 2 O or HOR). a. O HO HO OH O H 3 CO HO OH HOCH 3 /H + 3 (continued – Show the mechanism).
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Page 5 b. N H (H 3 C)
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