Use the relative bond lengths of the C%u2013C and C%u2013O bonds to predict whic

Question

Use the relative bond lengths of the C%u2013C and C%u2013O bonds to predict which of the following two equilibria in the picture lies farther to the right. (That is, predict which of the two compounds contains more of the conformation with the axial methyl group.)

A) The equilibrium of compound (1) lies farther to the right.

B) The equilibria of the two compounds are equal.

C) The equilibrium of compound (2) lies farther to the right.

Hint: Think about whether the difference between bond lengths of a C%u2013C bond and a C%u2013O bond will have a significant effect on the conformational equilibrium for each compound. Bond lengths: a C%u2013C bond is ~1.54 Angstroms and a C%u2013O bond is ~1.43 Angstroms.

Explanation / Answer

C) The equilibrium of compound (2) lies farther to the right.

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