ProblemSet3 - both configurational and stereoisomeric...

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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. Br 1 2 Look down C1-C2 (C1 in front) 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
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Unformatted text preview: both configurational and stereoisomeric (cis/trans). Be careful not to draw the same structure twice!!!!! 3) Consider the following structure. . NH 2 HO H H a) Clearly draw the compound shown in its most stable form (chair conformer). Clearly label the hydroxyl and amino groups as axial or equatorial. b) How many primary sp 3 carbons are present? c) How many secondary sp 3 carbons are present? d) How many tertiary sp 3 carbons are present? e) How many quaternary sp 3 carbons are present? (The terms primary, secondary, were not discussed in class, but are discussed in the textbook. You should add these descriptors to your organic vocabulary) 4) a) Provide IUPAC names for the following three structures b) Convert these IUPAC names to clear skeletal structures. 2-ethyl-1,1,4,4-tetramethylcyclohexane 4-ethyl-2,6-dimethylheptane 5) Draw both chair conformations for the cyclohexane structure shown, and clearly circle the most stable one. Cl...
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ProblemSet3 - both configurational and stereoisomeric...

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