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2011Exam1Key - CHEMISTRY 261 Exam 1 Dr Alexanian September...

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CHEMISTRY 261 Name_..::...\(.=-...;:{;'--'--C- ________ _ Exam 1 Dr. Alexanian Pledge: I have neither given nor received aid on this exam. September 23. 2011 1. Nomenclature (9 points) Either give the IUPAC name for compounds or provide the structure for the indicated name. Indicate R, S, cis, trans, where appropriate. a. b. c. ,Br .$' C\CI ~ ,. L _ '" c.lJ roc..,c.\·\r."",~ ... C2.. ( l!-~.<.:~s.J"" gre __ .. ",.- [S):1-chloro-3-methylpentane 2. Write valid Lewis structures for the following species. Show all non bonding (unshared) electrons and indicate any formal charges. (8 points). . . . 0 . H)~H 3. Explain why the following compound is not stable. (6 points) -\-,... ~ 't \- \:. .... l -.-, \to ....... .\ 0.. ...... , \ .... ~ \ Loe>,- ~-4t.. 4-0 r;"j. 4. Label the following as chiral or achiral. (2 pOints each) 1
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5. Draw the two chair conformations of cis-1 ,3-dimethylcyclohexane. One of these chair conformations is more stable by 5.4 kcal/mol. Given that a 1 ,3-diaxial interaction between a CH 3 and H atom is 0.9 kcal/mol, how much steric strain does a 1,3 diaxial interaction between two methyl groups introduce into the conformer? Show your calculations. (10 points) 5:.~ - O.C\ - 0.9 =.
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