Exam 1 -- Winter 2009 -- Blank

Exam 1 -- Winter 2009 -- Blank - W09 E1 Key I (24 points)...

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W09 E1 Key A. The penicillins are a class or antibiotics that have been of great importance in the development of modern medicine. One of these compounds, Penicillin V, is shown below. Provide the requested information about the Penicillin V structure. N S O N O O H H CH 3 CH 3 H O O H H ii) Circle the most acidic proton in Penicillin V. i) Assign the configuration to the three stereocenters by circling R or S . iii) Provide the hybridization of the two atoms indicated by the arrows. iv) Which of the following bases will completely remove (K eq > 10 3 ) the most acidic proton in Penicillin V ( circle the correct answer(s) ; no partial credit .) Na + Cl Na + OH O O CCl 3 Na + O Na + Na + H B. For the following pairs of structures, place an "x" in the box next to all TRUE statements. ( ) CH 3 H H 3 C H 1 CH 3 H 3 C H H 2 a) both 1 and 2 are optically active b) neither 1 nor 2 is chiral c) 1 and 2 are enantiomers d) 1 and 2 are diastereomers f) 1 and 2 are different conformations of the same molecule e) 1 and 2 are constitutional isomers i) a) both 3 and 4 are optically active b) neither 3 nor 4 is chiral c) 3 and 4 are enantiomers d) 3 and 4 are diastereomers f) 3 and 4 are different conformations of the same molecule e) 3 and 4 are constitutional isomers ii) CH 3 CH 2 CH 3 Cl H OCH 3 H 3 4 CH 2 CH 3 Cl H CH 3 OCH 3 H I ( 24 points ) or R or or Circle the most acidic proton in Penicillin V hybridization of S:
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This note was uploaded on 01/28/2011 for the course CHEM 210 taught by Professor Kiste during the Spring '10 term at Michigan Flint.

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Exam 1 -- Winter 2009 -- Blank - W09 E1 Key I (24 points)...

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