hrtest3bkey - Name THIRD HOUR TEST KEY 1. (21, 7 each) In...

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Third Hour Test (b), Chemistry 302, Fall 2004, Page 1 of 7 pages Name KEY THIRD HOUR TEST 1. (21, 7 each) In the spaces provided below, give the correct IUPAC names for the compounds having each of the following structures. a. 7-chloro-3-cyano-5-cyclopentyl-2-ethoxy-6-oxohept-3-enoyl chloride b. 5-amino-N-cyclohexyl-6-propoxy-N-propylcyclohepta-2,5-dienecarboxamide c. 1-ethyl-4-mercaptobut-2-ynyl 4-ethyl-6-hydroxyhex-4-enoate 2.(6) Pravachol ® , for which the structure is shown to the right, is one of the LDL (or “bad”) cholesterol lowering drugs known as “statins.” The final step in its synthesis, shown in simplified form below , is reaction of NaOH with a lactone to give the dihydroxycarboxylate product shown. Write the steps in the mechanism that accounts for opening the lactone under the conditions shown. REMEMBER: You may not add any other reagents. Be sure to show : (1) all intermediate structures that occur in the course of the mechanism, (2) any resonance structures that play a role in the process, (3) what, if anything, is added or lost at each step, and (4) all formal charges on the structures that you draw.
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Third Hour Test (b), Chemistry 302, Fall 2004, Page 2 of 7 pages 3. (21) When synthesizing peptides, which are similar to proteins but contain fewer amino acids, one of the common first step is to convert the carboxylic acid of an amino acid into a benzyl ester which can subsequently be removed by hydrogenolysis when required by the synthesis. Below is shown preparation of the benzyl ester of alanine hydrochlor- ide prior to its introduction into a peptide. Write the steps in the mechanism that accounts for the indicated reaction under the conditions shown. REMEMBER: You may not add any other reagents. Be sure to show : (1) all intermediate structures that occur in the course of the mechanism, (2) any resonance structures that play a role in the process, (3) what, if anything, is added or lost at each step, and (4) all formal charges on the structures that you draw.
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Third Hour Test (b), Chemistry 302, Fall 2004, Page 3 of 7 pages 4. (14) Starting with methyl cyclopentanecarboxylate and 4-methyl-1-pentene as the only sources of carbon atoms for the final product, show how to synthesize cyclopentylmethyl 3-methylbutanoate. You may use any other needed reagents or solvents so long as they do not contribute carbon atoms to the product. The reactions you use in each step should give the product you want as the major product of the reaction.
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This note was uploaded on 04/02/2008 for the course CHEM 301 taught by Professor Morrow during the Spring '08 term at New Mexico.

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hrtest3bkey - Name THIRD HOUR TEST KEY 1. (21, 7 each) In...

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