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Exam 2 -- Spring 2006 -- ANSWERS _do not distribute_

Exam 2 -- Spring 2006 -- ANSWERS _do not distribute_ - I(28...

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Name _______________________ Page 1 I. (28 points) A. Complete the following as necessary C C H 3 C + 2 equivalents of HBr i) NOTE: sp-hybridized carbanions make good nucleophiles for substitution reactions ii) a) C 6 H 12 Br 2 b) 1 H-NMR: 2 signals ratio: 1:3 c) 13 C-NMR: 4 signals a) C 6 H 12 Br 2 b) 1 H-NMR: 3 signals ratio: 1:2:9 c) 13 C-NMR: 4 signals + B. CH 3 CH 2 Br NaNH 2 CH 3 C H 3 C CH 3 C CH Product A Product B Would you expect product A in part ii) to be the major or minor product? Consider the following four structures when answering the questions below. Br Br Br Br H CH 3 Br H Br Br Compound C Compound D Compound E Compound F Write the letter(s) for the compound(s) that... i) ...is chiral ii) ...has at least one diastereomer iii) ...is a unique compound...no other stereoisomers exist i) ii) iii) iv) v) vi) iv) ...has at least one chiral diastereomer v) ...has an enantiomer vi) ...is meso NH 3 Na iii) 3 3 4 4 2 2 2 2 2 2 2 KEY C C H 3 C H C C H 3 C CH 2 CH 3 NaBr (optional) CH 3 C H 3 C CH 3 C CH 3 Br Br CH 3 C H 3 C CH 3 C CH Br Br H H minor E C,D,E F C,E E C
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H Name _______________________ Page 2 II. (26 points) A. CH 3 C OH H 3 C CH 3 Compound G Draw the two chair conformations for Compound G in the boxes below. Your drawings should clearly show both axial and equatorial positions for any ring atoms that have substituents ( be clear in your bond angles! ). What is the name of Compound G?
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