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Chapter 4 Discussion Section Problems

Chapter 4 Discussion Section Problems - a cis-1-ethyl-2- b...

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Chapter 4: Cycloalkanes Discussion Section Problems 1. Draw the two chair conformations of cis-1,3-dimethylcyclohexane and label all the positions as axial or equatorial. a. Label the higher energy and lower energy conformation b. The energy difference between these two conformers has been measured to be about 23kJ/mol (5.4 kCal/mol). How much of this energy is due to the torsional energy of gauche relationships? c. How much energy is due to the additional steric strain of the 1,3-diaxial interaction? 2. Draw the two chair conformations of each compound and label the substituents as axial and equatorial. In each case, determine which conformation is more stable.
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Unformatted text preview: a. cis-1-ethyl-2-isopropylcyclohexane b. cis-1-ethyl-3-methylcyclohexane c. cis-1-ethyl-4-methylcyclohexane d. trans-1-ethyl-2-isopropylcyclohexane e. trans-1-ethyl-3-methylcyclohexane 3. The most stable form of the common sugar glucose contains a six membered ring in the chair conformation with all the substituents equatorial. Draw the most stable conformation of glucose. 4. Trans-1,2-dimethylcyclobutane is more stable than cis-1,2-dimethylcyclobutane, but cis 1,3-dimethylcyclobutane is more stable than trans-1,3-dimethylcyclobutane. Use drawings to explain this observation....
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