Week_3.1_PurpleBook_Answers

Week_3.1_PurpleBook_ - 59 Cyclohexanes Week 3 1 Look at a chair Notice the axial and equatorial substituents Pay close attention to the parallel

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Cyclohexanes 2. Draw each of the following dimethyl cyclohexanes (on the planar ring), then identify whether the substituents would be either: "Axial and Equatorial" or "Both Equatorial" 1,2-cis 1,3-cis 1,4-cis 1,2-trans 1,3-trans 1,4-trans 3. Draw each of the following in the most stable chair conformation: 1. Look at a chair. Notice the axial and equatorial substituents. Pay close attention to the parallel lines! Ax. and Eq. Ax. and Eq. Ax. and Eq. Both Eq. Both Eq. Both Eq. Notice the confomation of that ethyl group: avoid syn-pentane! A chair has 3 sets of parallel lines, plus vertical lines for axial groups. Once that is drawn in, every subsequent line must be parallel to a line that has already ben drawn! Try drawing t-butyl groups in the equatorial positions. Week 3 59
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CH 3 3 CH 3 CH 3 H H Bicyclic Compounds and Bredt's Rule H H 1. Draw each of the following bicyclic compounds in a good "perspective" drawing. H H 2. The molecule trans -cyclooctene is known to exist. (It is chiral, by the way). Why is the analagous molecule -cyclohexene unstable? = -cyclooctene (planar representation) 3 CH 3 -cyclooctene (perspective representation) H 3 C 3 -cyclohexene???? 3. Draw each of the following bicyclic alkenes in a good "perspective" representation. Only one of these three compounds actually exists. Which one, and why? trans-decalin: two chairs norbornane skeleton: Far too strained to have a trans-alkene in a six-membered ring.
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This note was uploaded on 05/01/2008 for the course CHEM 51 taught by Professor Gribble during the Spring '08 term at Dartmouth.

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Week_3.1_PurpleBook_ - 59 Cyclohexanes Week 3 1 Look at a chair Notice the axial and equatorial substituents Pay close attention to the parallel

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