a) Calculate the difference in the Gibbs free energy between the second and first conformation including the algebraic sign. kJ/mol 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. %-

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry
Section4.SE: Something Extra
Problem 24VC: A trisubstituted cyclohexane with three substituents-red, green, and blue-undergoes a ring-flip to...
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Following are the alternative chair conformations for trans-1-bromo-2-methylcyclohexane:
Br
Br
CH3
ČH3
А
В
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:
axial → equatorial
AG° (kJ/mol) | Group
NH2
Group
AG° (kJ/mol)
C=N
-0.8
-5.9
Br
-2.4
CH3
-7.3
ОН
-3.9
1,2-gauche
3.8
a) Calculate the difference in the Gibbs free energy between the second and first conformation including the algebraic sign.
kJ/mol
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-'mol- and 298 K respectively.
Transcribed Image Text:Following are the alternative chair conformations for trans-1-bromo-2-methylcyclohexane: Br Br CH3 ČH3 А В 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: axial → equatorial AG° (kJ/mol) | Group NH2 Group AG° (kJ/mol) C=N -0.8 -5.9 Br -2.4 CH3 -7.3 ОН -3.9 1,2-gauche 3.8 a) Calculate the difference in the Gibbs free energy between the second and first conformation including the algebraic sign. kJ/mol 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-'mol- and 298 K respectively.
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