ProblemSet3(2) - CHEM 3570 FALL 2009 Problem Set 3 1 a Draw...

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CHEM 3570, FALL 2009 Problem Set 3 1) a) Draw Newman projections of the compound shown. You should be looking down the C1-C2 bond (C1 is the highest priority atom). Your first conformer should be one in which the Br (bromide) and the Me (methyl) are fully eclipsed. Rotate the rear carbon 60 degrees at a time and draw each resultant Newman projection. b) Using numbers (1,2,…,: 1=highest energy), rank each of the above conformer in terms of their relative energy. Where two conformers are of equal energy, give them the same number. Write your numbers below each conformer you drew in part a. c) Draw an energy versus dihedral angle (rotation) diagram for a complete rotation around the indicated bond showing the relative energy levels of all of your conformers. Make the y-axis energy and the x-axis the dihedral angle. Start your diagram with the conformer you labeled as #1 in part b). 2) Clearly draw ALL possible dimethyl cyclopentane structures including both configurational and stereoisomeric (cis/trans). Be careful not to draw the same structure twice!!!!!
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