The two alternative chair conformations of cis-1-cyano-4-methylcyclohexane differ in their Gibbs free energy. Using the data for ΔG° for monosubstituted cyclohexanes at room temperature (25ºC): Axial → Equatorial Group ΔG° (kJ/mol) Group ΔG° (kJ/mol) C-N triple bond −0.8 NH2 −5.9 Br −2.4 CH3 −7.3 OH −3.9 1,2-gauche +3.8 calculate the absolute value of the difference in the Gibbs free energy between the alternative chair conformations.

The two alternative chair conformations of cis-1-cyano-4-methylcyclohexane differ in their Gibbs free energy. Using the data for ΔG° for monosubstituted cyclohexanes at room temperature (25ºC): Axial → Equatorial Group ΔG° (kJ/mol) Group ΔG° (kJ/mol) C-N triple bond −0.8 NH2 −5.9 Br −2.4 CH3 −7.3 OH −3.9 1,2-gauche +3.8 calculate the absolute value of the difference in the Gibbs free energy between the alternative chair conformations.

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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Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

The two alternative chair conformations of cis-1-cyano-4-methylcyclohexane differ in their Gibbs free energy.

Using the data for ΔG° for monosubstituted cyclohexanes at room temperature (25ºC):

Axial → Equatorial
Group	ΔG° (kJ/mol)	Group	ΔG° (kJ/mol)
C-N triple bond	−0.8	NH2	−5.9
Br	−2.4	CH3	−7.3
OH	−3.9	1,2-gauche	+3.8

calculate the absolute value of the difference in the Gibbs free energy between the alternative chair conformations.

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