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In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.

Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered ethane, the bonding molecular orbital of one C-H bond interacts with the antibonding molecular orbital of the other, thereby further stabilizing the conformation. The rotation of farther carbon while keeping the carbon nearer to the observer stationary generates an infinite number of conformers. At 0° dihedral angles, the C-H groups cover one another to form an eclipsed conformation. This conformation has about 12 kJ/mol more torsional strain than the staggered conformation and hence is less stable. Ethane molecules rapidly interconvert between several staggered states while passing through the higher energy eclipsed states. The molecular collisions provide the energy required to cross this torsional barrier.

Similar to ethane, propane also has two major conformers: the stable staggered conformer (low energy) and the unstable eclipsed conformer (higher energy).

Tags

ConformationsEthanePropaneOrganic MoleculeCarbon carbon Single BondRotationInternal RotationStaggered ConformationEclipsed ConformationTorsional StrainBonding Molecular OrbitalAntibonding Molecular OrbitalDihedral AnglesTorsional Barrier

Aus Kapitel 3:

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3.6 : Conformations of Ethane and Propane

Alkanes and Cycloalkanes

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3.1 : Structure of Alkanes

Alkanes and Cycloalkanes

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3.2 : Constitutional Isomers of Alkanes

Alkanes and Cycloalkanes

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3.3 : Nomenclature of Alkanes

Alkanes and Cycloalkanes

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3.4 : Physical Properties of Alkanes

Alkanes and Cycloalkanes

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3.5 : Newman Projections

Alkanes and Cycloalkanes

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3.7 : Conformations of Butane

Alkanes and Cycloalkanes

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3.8 : Cycloalkanes

Alkanes and Cycloalkanes

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3.9 : Conformations of Cycloalkanes

Alkanes and Cycloalkanes

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3.10 : Conformations of Cyclohexane

Alkanes and Cycloalkanes

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3.11 : Chair Conformation of Cyclohexane

Alkanes and Cycloalkanes

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3.12 : Stability of Substituted Cyclohexanes

Alkanes and Cycloalkanes

12.1K Ansichten

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3.13 : Disubstituted Cyclohexanes: cis-trans Isomerism

Alkanes and Cycloalkanes

11.5K Ansichten

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3.14 : Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes

Alkanes and Cycloalkanes

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