Required Homework Sheet

Chapter 4



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1. Using conformational analysis techniques, develop a relative energy diagram for the stated bonds on the following compounds. Use Table 4.1 on page 114 as a source for eclipsing interactions. In cases where carbon groups other than methyl groups are needed (i.e. ethyl group), use the value for the methyl group. Additionally, assume all gauche interactions to be 0.9 kcal/mol. (15 points)

C(2)-C(3) bond of pentane

























C(2)-C(3) bond of 3-methylpentane

























C(2)-C(3) bond of 2,3-dimethylbutane

























2. Draw the most stable chair conformation for the following cycloalkanes. Use Table 4.2 on page 132 for the 1,3-diaxial interactions. As with the previous problem, assume all gauche interactions to be 0.9 kcal/mol. (9 points)

Cis-1-bromo-2-chlorocyclohexane















Trans-1-chloro-3-methylcyclohexane

















Cis-1-ethyl-4-methylcyclohexane