ollowing are the alternative chair conformations for trans-2-methylcyclohexanamine: NH₂ Group C=N Br CH3 B Using the data for AG for monosubstituted cyclohexanes at room temperature (25°C) and the representative value for the gauche interaction of two equatorially positioned substituents in the 1,2-position: OH axial AG (kJ/mol) -0.8 -2.4 CH3 -3.9 -NH₂ equatorial Group NH₂ CH3 1,2-gauche AG (kJ/mol) -5.9 -7.3 3.8 a) Calculate the difference in the Gibbs free energy between the second and first conformation including the algebraic sign. b) Given your value in (a), calculate the percent of the chair, indicated as B, presented in an equilibrium mixture of the conformers at 25°C. *The actual value will depend on the substituents. The values of the gas constant and the temperature for 25°C are 8.314 JK mol¹ and 298 K respectively. kJ/mol %

ollowing are the alternative chair conformations for trans-2-methylcyclohexanamine: NH₂ Group C=N Br CH3 B Using the data for AG for monosubstituted cyclohexanes at room temperature (25°C) and the representative value for the gauche interaction of two equatorially positioned substituents in the 1,2-position: OH axial AG (kJ/mol) -0.8 -2.4 CH3 -3.9 -NH₂ equatorial Group NH₂ CH3 1,2-gauche AG (kJ/mol) -5.9 -7.3 3.8 a) Calculate the difference in the Gibbs free energy between the second and first conformation including the algebraic sign. b) Given your value in (a), calculate the percent of the chair, indicated as B, presented in an equilibrium mixture of the conformers at 25°C. *The actual value will depend on the substituents. The values of the gas constant and the temperature for 25°C are 8.314 JK mol¹ and 298 K respectively. kJ/mol %

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter2: Alkanes And Cycloalkanes

Section: Chapter Questions

Problem 2.45P: Gibbs free energy differences between axial-substituted and equatorial-substituted chair...

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Compounds 1 and 2 were prepared, and the difference in their heats of combustion was found to be 17.2 kJ/mol (J. Am. Chem. Soc. 1961, 83, 606-614): H H 1 Shown below are the lowest-energy conformations of compounds 1 and 2. Identify which drawing matches which compound, and identify which compound has the larger heat of combustion. H H H H |||I 2 H 4 H H The first drawing is compound 1, and compound 1 has a larger heat of combustion because it is the less stable compound. O The first drawing is compound 2, and compound 2 has a larger heat of combustion because it is the less stable compound. The first drawing is compound 2, and compound 2 has a larger heat of combustion because it is the more stable compound. The first drawing is compound 1, and compound 1 has a larger heat of combustion because it is the more stable compound.
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