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Homework4 - Newman Projection Practice 1 Organic Chemistry...

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Newman Projection Practice 1 Organic Chemistry I – Jasperse Newman Projection Practice A. For each of the following, draw the best and worst Newman projection, relative to the bond indicated. 1. Butane, relative to the C2-C3 bond 2. 1-chloropropane, relative to the C1-C2 bond 3. 2-methylbutane, relative to the C2-C3 bond 4. 2,2-dimethylbutane, relative to the C2-C3 bond 5. 2-chloro-2-methylpentane, relative to the C2-C3 bond Note: Cl is smaller than methyl B. Rotation Barriers. 6. Rank the rotation barriers relative to the indicated bonds, with 1 have the largest barrier For convenience, Et = ethyl and iPr = isopropyl Assume that a halogen, OH, or NH 2 is smaller than a CH 3 or any other alkyl group. Et Et Cl iPr Et Et iPr Et Et (See page 4 for some summary of operations/steps for handling Newman projections)
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Newman Projection Practice 2 C. For each of the following, use the words torsional and/or steric to explain why the first conformation is more stable than the second. (The answer key and explaining video will be a bit more detailed as appropriate.) a. For each, note if any “total eclipse” steric interactions exist (two non-hydrogens eclipsing) b. For each, note if any “gauche” steric interactions exist (two non-hydrogens gauche) 7. H CH 3 H H CH 3 H H CH 3 H CH 3 H H 8. H CH 3 H H CH 3 H H CH 3 H H CH 3 H 9. H CH 3 H H CH 3 H H CH 3 H CH 3 H H 10.
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