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Following are the alternative chair conformations for trans-1-bromo-2-methylcycl

ID: 2127757 • Letter: F

Question

Following are the alternative chair conformations for trans-1-bromo-2-methylcyclohexane: 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: Calculate the difference in the Gibbs free energy between the second and first conformation including the algebraic sign kJ/mol 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 %

Explanation / Answer

a) ?G = -2.4+ (-7.3) = - 9.7 kJ/mol (adding representative value* for the gauche interaction of two equatorially positioned substituents in the 1,2-position)

b) ?G = - RT lnK = -9.7 kJ/mol

- (8.314 J/Mol K)* (298 K) * lnK = -9.7 * 1000 J/mol

ln K = 3.915

K = e ^ (3.915) = 50 = [product] / [reactant] = [B]/[A]

ie B = 50 A

% B= B / (B+A) = 50A / (50 A+ A) = 50 / 51 = 0.9804 = 98.04%