Exercises4-1 - CHAPTER 4 1) a) Draw a Newman projection of...

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Unformatted text preview: CHAPTER 4 1) a) Draw a Newman projection of all the different staggered and eclipsed conformations of the 1,2-dichloroethane. b) Which conformation has the largest dipole moment ? c) Which conformation has the smallest dipole moment ? d) What should be the value of the dipole moment of the 1,2-dichloroethane at very low temperature? 2) a) Draw the two chair conformations of the cis-1,4-dichlorohexane, and circle the more stable conformer. b) Draw the two chair conformations of the trans-1,4-dichlorohexane, and circle the more stable conformer. c) Which is the more stable isomer? 3) Draw the two chair conformations of the following compound. Knowing that the strain due to an H…F 1,3-diaxial interaction is equal to 0.5 kJ/mol, while the strain due to an H…CO2H 1,3-diaxial interaction is equal to 2.9 kJ/mol, circle the more stable conformer. F CO2H 4) There are several possible isomers for the the 1,2,3,4,5,6-hexamethylhexane. Draw the more stable chair conformation of the more stable isomer. Then, draw the more stable isomer, using a representation as above (solid lines for the ring, and dash and heavy wedged lines to indicate the stereochemistry) ...
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