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CHM 151 (PS 2 F07)

CHM 151 (PS 2 F07) - CHM 151(HLS Problem Set 2 CHEMISTRY...

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CHM 151 (HLS); Problem Set 2 1 CHEMISTRY 151.001 Fall 2007 Problem Set 2 September 10-14 1. Consider the following three conformations. a. Calculate the strain energy associated with each using the values in the attached table. Specify the kinds of strain contributing to the overall energy of the conformer. b. Are the three molecules conformational isomers, constitutional isomers, or not isomers at all? c. If there is a more stable conformation of one or all draw it clearly using the sawhorse notation and Newman projection. Type of Interaction Energy Increase H, H eclipsing 0.9 H, CH 3 eclipsing 1.5 CH 3 , CH 3 eclipsing 4 CH 3 , CH 3 gauche 0.9 H 3 C H H H CH 3 H 3 C dihedral angle = 0 CH 3 H CH 3 CH 3 H H 3 C H H CH 3 CH 3 CH 3 H
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CHM 151 (HLS); Problem Set 2 2 2. For each of the following substituted cyclohexanes, show both chair conformational isomers and indicate which one would predominate at room temperature given that the size of the various substituents increases in the order indicated.
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