Question

Look at the effects of strain on C-C bond lengths. Butane: 1.535 v. 1.520 and t-butylcyclohexane:...

Look at the effects of strain on C-C bond lengths. Butane: 1.535 v. 1.520 and t-butylcyclohexane: 1.581 (axial) v. 1.575(equitorial). Explain the change in bond length between these structures.

Homework Answers

Answer #1

The bond lengths in butane: C2-C3 bond distance (eclipsed) = 1.535
C1-C2 bond distance (eclipsed) = 1.520

due to -CH3 and -CH3 group steric interaction in the case of eclipsed leads to C2-C3 bond distance (eclipsed) = 1.535 but in case of   C1-C2 bond distance (eclipsed) , there is only one -CH2CH3 and -H group interaction.

The bond lengths in t-butylcyclohexane: C-CMe3 bond length (axial) = 1.581
C-CMe3 bond length (equatorial) = 1.575

C-CMe3 bond length (axial) = 1.581, because at the axial position the 1,3-diaxial interaction between tert-but and H group leaads to a longer bond leght but C-CMe3 bond length (equatorial) = 1.575 due to no steric hinderance.

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