Chapter 2: Problem 58
Following are structural formulas and heats of combustion of acetaldehyde and
ethylene oxide. Which of these compounds is more stable? Explain.
Chapter 2: Problem 58
Following are structural formulas and heats of combustion of acetaldehyde and
ethylene oxide. Which of these compounds is more stable? Explain.
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Get started for freeFrom studies of the dipole moment of 1,2 -dichloroethane in the gas phase at room temperature \(\left(25^{\circ} \mathrm{C}\right)\), it is estimated that the ratio of molecules in the anti conformation to gauche conformation is \(7.6\) to 1 . Calculate the difference in Gibbs free energy between these two conformations.
Each member of the following set of compounds is an alcohol; that is, each
contains an - OH (hydroxyl group, Section 1.3A). Which structural formulas
represent the same compound? Which represent constitutional isomers?
(a)
\(1,2,3,4,5,6\)-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.
There are four cis, trans isomers of 2 -isopropyl-5-methylcyclohexanol:
Which would you predict to have the larger (more negative) heat of combustion, cis-1,4-dimethylcyclohexane or trans- 1,4 -dimethylcyclohexane?
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