Chapter 2: Problem 7
Following are the structural formulas and names of four bicycloalkanes. Write the molecular formula of each compound. Which of these compounds are constitutional isomers?
Chapter 2: Problem 7
Following are the structural formulas and names of four bicycloalkanes. Write the molecular formula of each compound. Which of these compounds are constitutional isomers?
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Get started for free\(1,2,3,4,5,6\)-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans3,6-hexachlorocyclohexane. (a) Draw a structural formula for \(1,2,3,4,5,6\)-hexachlorocyclohexane disregarding, for the moment, the existence of cis,trans isomerism. What is the molecular formula of this compound? (b) Using a planar hexagon representation for the cyclohexane ring, draw a structural formula for lindane. (c) Draw a chair conformation for lindane and label which chlorine atoms are axial and which are equatorial. (d) Draw the alternative chair conformation of lindane and again label which chlorine atoms are axial and which are equatorial. (e) Which of the alternative chair conformations of lindane is more stable? Explain.
Draw the alternative chair conformations for the cis and trans isomers of 1,2 -dimethylcyclohexane, 1,3 -dimethylcyclohexane, and 1,4 -dimethylcyclohexane. (a) Indicate by a label whether each methyl group is axial or equatorial. (b) For which isomer(s) are the alternative chair conformations of equal stability? (c) For which isomer(s) is one chair conformation more stable than the other?
What generalization can you make about the densities of alkanes relative to the density of water?
When cyclohexane is substituted by an ethynyl group, \(-\mathrm{C} \equiv \mathrm{CH}\), the energy difference between axial and equatorial conformations is only \(1.7 \mathrm{~kJ}(0.41 \mathrm{kcal}) / \mathrm{mol}\). Compare the conformational equilibrium for methylcyclohexane with that for ethynylcyclohexane and account for the difference between the two.
Following are the alternative chair conformations for trans-1,2-dimethylcyclohexane. (a) Estimate the difference in free energy between these two conformations. (b) Given your value in (a), calculate the percent of each chair present in an equilibrium mixture of the two at \(25^{\circ} \mathrm{C}\).
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