Name the above compound, identify each substitutent as axial or equatorial, and tell whether the conformation shown is the more stable or less stable form.
Omit customary italics from your name.
Substitutents R1 and R2 are designated in the order they appear in the IUPAC name. Axial/equatorial strain energy increments are available in the table below.
The IUPAC name is
Position of R1 _________axial or equatorial. Position of R2 _________axial or equatorial
The conformation shown is the _________more stable or less stable.
Axial Strain Energies for Monosubstituted Cyclohexanesa,b
Substituent (solvent)
kJ/mol
kcal/mol
Substituent (solvent)
kJ/mol
kcal/mol
-CH3
7.3
1.7
-CO2CH2CH3
5.0
1.2
-CH2CH3
7.5
1.8
-Cl
2.5
0.6
-CH(CH3)2
9.2
2.2
-Br
2.5
0.6
-C(CH3)3
20
4.8
-CN, cyano
0.8
0.2
phenyl
11.7
2.8
-OH (cyclohexane)
2.5
0.6
cyclohexyl
9.2
2.2
-OH (isopropanol)
4.0
1.0
-CH=CH2
6.2
1.5
-OCH3
2.5
0.6
-CCH, ethynyl
2.1
0.5
-NH2 (toluene)
5.2
1.2
-CHO
3.0
0.7
-NH2 (CH3OCH2CH2OH/H2O)
7.1
1.7
-COCH3
5.1
1.2
-NO2
4.8
1.1
-CO2H
5.9
1.4
Energy difference between axial and equatorial conformers.
Solvent specified when the increment is solvent dependent.
