chem118AF09FinalKey

chem118AF09FinalKey - Chem 118A, Fall 2008, Final Exam key...

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(1) (15 points total) Please identify each of the following pairs of molecules as either: A : constitutional isomers B : stereoisomers (in which case you must also indicate if they are enantiomers or diastereomers) C : different representations of the same molecule D : not the same molecule, but also not isomers Chem 118A, Fall 2008, Final Exam _______________________________ name Br H H 3 C H 3 C H CH 2 CH 2 CH 3 Br Cl F Cl F Cl F Cl F O O Cl O O Cl key different representations of different representations of not the same molecule, but also not isomers
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Chem 118A, Fall 2008, Final Exam _______________________________ name (2) (25 points total) Shown below is a molecule called batrachotoxin, one of the most toxic substances known, along with the poison dart frog that secretes it when agitated. (a) On the structure of batrachotoxin shown above, please identify each oxygen atom as part of an alcohol (also note whether it is primary, secondary or tertiary), an ether, a ketone, an aldehyde, an ester, an amide, or a carboxylic acid. (b) Please identify the hybridization a n d geometry of the two atoms marked with symbols. (c) Please assign an appropriate R / S label to the stereocenter marked with a # symbol. (d) Two protons are marked with @ symbols. Which of these two sites is more acidic? Please explain your reasoning clearly. * * * @ 2 @ 1 O OH O N O O N H H key ester ether alcohol (tertiary) sp 2 trigonal planar 3 tetrahedral @ 1 is the more acidic site. Unlike for the @ 2 site, deprotonation at the @ 1 sitre leads to a conjugate base that is stabilized by resonance: R' R O N R" R' R O N R"
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H (3) (20 points total) Please explain (clearly and concisely) why the chair form of cyclohexane is less strained (on a per carbon basis) than cyclopropane. Your answer should include drawings of these molecules that clearly show their 3-dimensional shape.
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chem118AF09FinalKey - Chem 118A, Fall 2008, Final Exam key...

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