How can I solve this problem? Choices for Part b: methyl, OH, Br, CN, amino The

Question

How can I solve this problem?

Choices for Part b: methyl, OH, Br, CN, amino

The two alternative chair conformations of ck-4-mcthyIcyclohcxanaminc differ in their Gibbs free energy. Using the data for AG (Axial-Equatorial) for monosubstituted cyclohexanes at room temperature (25 degree C): Calculate the absolute value of the difference in the Gibbs free energy between the alternative chair conformations. Which group in this compound is in axial position in the energetically preferred chair conformation?

Explanation / Answer

Cis 4 means two groups CH3 and NH2 occupy axial equitorial or equitiorial and axial positions repectively.

Enegry change for methyl at axial to equitorial and NH2 at equitorial to axial = ( -7.3) -( 5.9) = -1.4 KJ/mol

b) Br is favored , since there will be axial H of adjacent carbon and Br electrostatic interactions ( attraction) which makes relatively stable compared to others

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