E1W09KEY215 - W09 E1 Key W09 215 E1 Name I(24 points A The...

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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. ( no partial credit ) 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 ) R or S R or S R or S Circle the most acidic proton in Penicillin V hybridization of S: sp 3 expected hybridization of N: sp 2 a b c d e f X X a b c d e f X X 6 2 4 4 4 4 2 each box or circle W09 215 E1 Name:________________________________
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W09 E1 Key A. ( JOC , 74 , 2009) Two reactions (Molecule A to Molecule B and Molecule B to Molecule C) are shown. In Molecule A, circle any atom/s whose oxidation numbers change in the formation of B. In Molecule B, circle any
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