Strain Energy Increments
For Alkanes:
Interaction / Compound kJ/mol kcal/mol
H : H eclipsing 4.0 1.0
H : CH3 eclipsing 5.8 1.4
CH3 : CH3 eclipsing 11.0 2.6
gauche butane 3.8 0.9
cyclopropane 115 27.5
cyclobutane 110 26.3
cyclopentane 26.0 6.2
cycloheptane 26.2 6.3
cyclooctane 40.5 9.7
Axial Strain Energies for Monosubstituted Cyclohexanes:a,b
Substituent(solvent) kJ/mol kcal/mol
-CH3 7.3 1.7
-CH2CH3 7.5 1.8
-CH(CH3)2 9.2 2.2
-C(CH3)3 20 4.8
phenyl 11.7 2.8
cyclohexyl 9.2 2.2
-CH=CH2 6.2 1.5
-CCH, ethynyl 2.1 0.5
-CHO 3.0 0.7
-COCH3 5.1 1.2
-CO2H 5.9 1.4
-CO2CH2CH3 5.0 1.2
-Cl 2.5 0.6
-Br 2.5 0.6
-CN, cynao 0.8 0.2
-OH (cyclohexane) 2.5 0.6
-OH (isopropanol) 4.0 1.0
-OCH3 2.5 0.6
-NH2 (toluene) 5.2 1.2
-NH2 (CH3OCH2CH2OH/H2O) 7.1 1.7
-NO2 4.8 1.1
a. Energy difference between axial and equatorial conformers.
b. Solvent specified when the increment is solvent dependent.
Data from "Stereochemistry of Organic Compounds", E. L. Eliel and S. H.
Wilen, John Wiley, New York, NY, 1994.
Chemistry Homework Solutions
#8418
Confirmation of a derivative of cyclohexane
Confirmation of a derivative of cyclohexane
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