KEYPre#3-251-06 - ORGANIC CHEMISTRY LECTURE CHY 251(02)...

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ORGANIC CHEMISTRY LECTURE CHY 251(02) Prelim III, 11/16/06 _______ KEY _______ I. Each of the following multiple choice questions has one correct answer. (3pts/each) 1. How many chirality (stereogenic) centers are found in the structure of dysidiolide, below? a) 1 b) 2 c) 3 d) 4 e) 5 f) 6 H 3 C O O HO HO H 3 C CH 3 CH 3 CH 2 2. Which one of the following is optically inactive ? H CO 2 H C C C Et H H Et H H 3 C NH 2 H 2 N H 3 C CH 3 H H a) b) c) d) CH 2 CH 3 CH 2 CH 2 CH 3 HO CH 3 3. Which one of the following compounds has the S configuration ? CO 2 H CH 3 H 2 N H Et H HS H 3 C OCH 3 Et H HO CH 3 CHO Br Et a) b) c) d) Et CH 3 Br H 3 C e) * 4. What is the total number of stereoisomers that can form from CH 3 -CHBr-CH=CH-CH 3 ? a) 2 b) 4 c) 6 d ) 8 e) 10
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5. Bromine addition to cis -2-butene in chloroform affords _ _ _ _ _ as the final product. a) ( Z )-2-bromo-2-butene b) ( E )-2-bromo-2-butene c) (+)-2,3-dibrombutane d) (-)-2,3-dibrombutane e) meso -2,3-dibromobutane f) racemic -2,3-dibromobutane 6. If one mole of each of the following alkenes is subjected to complete combustion in a pure oxygen atmosphere, which one would liberate the least amount of heat ? a) 1-pentene b) 2-pentene c) 2-methyl-1-butene d) 2-methyl-2-butene e) 3-methyl-1-butene f) cyclohexene 7. Which one of the following alkenes would afford a racemic mixture upon addition of HBr? CH 3 H CH 3 C H CH 2 Cl H C CH 2 H 3 C H a) b) c) d) 8. Which one of the following is an incorrect statement ( not true) about enantiomers ? a) Enantiomers have the same melting point. b) Enantiomers have the same proton and carbon-13 NMR spectra. c) Enantiomers have the same chemical reactivity with non-chiral reagents. d) Enantiomers have the same specific rotation. e)
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This test prep was uploaded on 04/18/2008 for the course CHY 251 taught by Professor Jensen during the Fall '06 term at University of Maine Orono .

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KEYPre#3-251-06 - ORGANIC CHEMISTRY LECTURE CHY 251(02)...

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