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Exam 2 Key - CHM 110 Fall 2013 Exam 2 ALL ANSWERS MUST BE...

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1 CHM 110 Fall 2013 Exam 2 ** ALL ANSWERS MUST BE WRITTEN IN INK ** Name: Please read all questions very carefully. 1. Name the following compounds (4 points): ( S )-5-bromo-5-chlorohex-2-yne ( E )-5-ethyl-6-methyloct-3-ene 2. The molecule Atorvastatin (commonly known as Lipitor) had $13.3 billion dollars in sales last year. Circle all the stereocenters/chiral carbons ( make sure that each circle is around a single atom ) (4 points)
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2 3. Of the four structures below, circle the most acidic (3 points): 4. For the following reactions, determine whether the pre-dominant mechanism is either S N 1 , S N 2, E1, or E2 (12 points)?
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3 5. State the relationship between the following molecules as enantiomers, diastereomers, identical, or constitutional isomers (10 points). H CH 3 OH CO 2 H Br I Cl I Br Cl CO 2 H H OH CH 3 I Br Cl Br Cl I O Cl H O H Cl H H a) b) c) d) H e) H H enantiomers constitutional isomers identical enantiomers diastereomers
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4 6. [1-step synthesis problems] Write the structure of the compound consistent with the specified information (12 points).
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Exam 2 Key - CHM 110 Fall 2013 Exam 2 ALL ANSWERS MUST BE...

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