Following are the alternative chair conformations for trans-2-bromocyclohexanami

Question

Following are the alternative chair conformations for trans-2-bromocyclohexanamine: Using the data for G for monosubstituted cyclohexanes at room temperature (25 degree C) and the representative value* for the gauche interaction of two equatorially positioned substituents in the 1,2-position: 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 degree C. *The actual value will depend on the substituents. The values of the gas constant and the temperature for 25 degree C are 8.314 JK^-1 mol^-1 and 298 K respectively.

Explanation / Answer

a) The difference in delta G

For diaxial A = -5.9 - 2.4 = -8.3 kJ/mol

For equatorial = +3.8 kJ/mol

difference delta G = -8.3 + 3.8 = -4.5 kJ/mol

b) percent of B = 84.44 %

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