exam 2 ochem

exam 2 ochem - Chemistry Department University of Alberta...

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Chemistry Department University of Alberta CHEM 161 Exam II November 8, 2005 1. The following table lists the steric strain due to one hydrogen - substituent 1,3-diaxial interaction in some monosubstituted cyclohexanes: Substituent Strain (kJ/mol) -Cl 1.0 -OH 2.1 -CH 3 3.8 -CH(CH 3 ) 2 4.6 -C(CH 3 ) 3 11.4 a. Draw the most stable conformation of trans -1-chloro-3- methylcyclohexane:
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Justify your decision using the principles of conformational analysis. Both possible conformations are free of angle strain and of torsional strain. However the steric strain due to two H – Cl 1,3-diaxial interactions is 2.0 kJ/mol whereas that due to two H – CH 3 1,3-diaxial interactions is 7.6 kJ/mol c. One of the two chair structures of cis -1-chloro-3- methylcyclohexane is more stable than the other by 15.5 kJ/mol. Draw the structure of the more stable structure. d. Calculate the energy cost of a 1,3-diaxial interaction between a chlorine and a methyl group. 15.5 - 1.0 – 3.8 = 10.7 kJ/mol
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exam 2 ochem - Chemistry Department University of Alberta...

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