322BSpring_09_4TH_PRACTICE - 322b Fourth Practice...

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322b Fourth Practice Test (Chapters 21,22, 23) Spring 2009 1. Write the structure (choose your own example) a. Ester b. Lactam c. Oxime d. Sulfonamide e. Thioacetal f. Osazone g. Imide h. Carbamate i. Dialkyl carbonate 2. Write the mechanisms of: a. N BuLi N Bu + LiH b. c. f. O O OH +CH 3 CO 2 H Br OH - ! ONa + O HC(O)(CHOH) 3 CH 2 OH OH - H 2 O HC(O)CH 2 OH + HC(O)CHOHCH 2 OH O O H 3. A D-Aldopentose upon oxidation with HNO 3 gives an optically active aldaric acid. The Ruff degradation (1) Br 2 /H 2 O, (2) CaCO 3 and heat, (3) H 2 O 2 /Fe 3 + of the aldopentose gives a D-Aldotetrose that is oxidized to give meso tartaric acid. Write the Fisher structure of the aldopentose. Show your reasoning.
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2 4. a) Arrange in order of basicity starting with most basic compound: O O O 2 N O O 2 N NO 2 O O 2 N O 2 N O 2 N NO 2 NO 2 O (a) (b) (c) (d) (e) b) Arrange in order of acidity starting with most acidic compound: OH OH CH 3 O OH OH OH H OH CH 2 OH (a) (d) (c) (b) 5. Choose the relationship that
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322BSpring_09_4TH_PRACTICE - 322b Fourth Practice...

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