Exam3_S98 - 1. page 1 of 6. Give the product of the...

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Unformatted text preview: 1. page 1 of 6. Give the product of the following reactions. The stereochemistry of the reactant is as shown. Give the proper sterochemistry of the major stereoisomer of the product. (20 pts) CpCo(CO)2 R R NHBn CHO I2 CO2 H H H2 , Pd/C O N H CH3 O N O O a) Bu2BOTf, Et3N b) PhCHO Ph 2. page 2 of 6. Give the reagent(s) necessary to carry out the following transformations. The stereochemistry of the products and reactants is as shown. (20 pts) Ph CHO Ph OH O OBn OBn OBn OH CH3 OBn O CO 2H O OMe OMe Me O OH O OMe O OH OEt O I O OEt CN page 3 of 6. 3. Short Answers. (5 points each, 20 points total) a. Define enantioselective and enantiospecific and give examples of each. b. What is the Stork-Eschenmoser hypothesis? page 4 of 6. c. What are Baldwin's Rules (be general, do not give each specific rule)? Be sure to explain what are the basis of the rules and give one example each of a reaction that is favored and disfavored according to Baldwin's rule. d. Define umpolung and give an example. page 5 of 6. 4. Provide the product and all intermediates for the following sequence of reactions. (20 pts) 1) (CH3)2 C(OCH3)2 , H+ 2) MnO2 3) (EtO)2P(O)CH2 CO 2Me, base 4) AcOH, THF, H2 O OH 5) tBuSiCl (1 equv), pyridine 6) TsCl, pyridine 7) Bu4NF OH OH 5. page 6 of 6. Complete the synthesis for the target shown. Give all reagents and intermediates. (20 pts). O ~ 6 steps O OBn O ...
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This note was uploaded on 03/11/2012 for the course CHEM 233 taught by Professor Staff during the Fall '10 term at Vanderbilt.

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Exam3_S98 - 1. page 1 of 6. Give the product of the...

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