Gibbs free energy differences between axial-substituted and equatorial-substituted chair conformations of cyclohexane were given in Table 2.4.Q. Calculate the ratio of equatorial to axial tert-butylcyclohexane at 25°C. Table 2.4 AG° (Axial-Equatorial) for Monosubstituted Cyclohexanes at 25°Caxial → equatorial-AG-AGGroupkJ/molkcal/molGroupkJ/molkcal/molC=N0.80.19NH,5.91.41F1.00.24СООН5.91.41C=CH1.70.41C=CH,7.11.701.90.45CH,7.281.74CI0.53CH,CH,CH(CH,),2.27.31.75Br2.40.579.02.15OH3.90.93C(CH,),21.05.00

The tert-butyl cyclohexane can occupy either axial or equatorial position. But due to its bulkiness,…

Table 2.4 AG° (Axial-Equatorial) for Monosubstituted Cyclohexanes at 25°C axial → equatorial -AG -AG Group kJ/mol kcal/mol Group kJ/mol kcal/mol C=N 0.8 0.19 NH, 5.9 1.41 F 1.0 0.24 СООН 5.9 1.41 C=CH 1.7 0.41 C=CH, 7.1 1.70 1.9 0.45 CH, 7.28 1.74 CI 0.53 CH,CH, CH(CH,), 2.2 7.3 1.75 Br 2.4 0.57 9.0 2.15 OH 3.9 0.93 C(CH,), 21.0 5.00

Table 2.4 AG° (Axial-Equatorial) for Monosubstituted Cyclohexanes at 25°C axial → equatorial -AG -AG Group kJ/mol kcal/mol Group kJ/mol kcal/mol C=N 0.8 0.19 NH, 5.9 1.41 F 1.0 0.24 СООН 5.9 1.41 C=CH 1.7 0.41 C=CH, 7.1 1.70 1.9 0.45 CH, 7.28 1.74 CI 0.53 CH,CH, CH(CH,), 2.2 7.3 1.75 Br 2.4 0.57 9.0 2.15 OH 3.9 0.93 C(CH,), 21.0 5.00

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry

Section4.SE: Something Extra

Problem 40AP: From the data in Figure 4-12 and Table 4-1, estimate the percentages of molecules that have their...

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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

Gibbs free energy differences between axial-substituted and equatorial-substituted chair conformations of cyclohexane were given in Table 2.4.

Q. Calculate the ratio of equatorial to axial tert-butylcyclohexane at 25°C.

Table 2.4 AG° (Axial-Equatorial) for Monosubstituted Cyclohexanes at 25°C
axial → equatorial
-AG
-AG
Group
kJ/mol
kcal/mol
Group
kJ/mol
kcal/mol
C=N
0.8
0.19
NH,
5.9
1.41
F
1.0
0.24
СООН
5.9
1.41
C=CH
1.7
0.41
C=CH,
7.1
1.70
1.9
0.45
CH,
7.28
1.74
CI
0.53
CH,CH,
CH(CH,),
2.2
7.3
1.75
Br
2.4
0.57
9.0
2.15
OH
3.9
0.93
C(CH,),
21.0
5.00

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