Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 5, Problem 5.28P
Interpretation Introduction

Interpretation:

Bond angle of CCC and CCH of cis and trans-isomers of cyclooctene has to be measured and compared with the bond angle predicted using VSEPR theory. The isomer with higher bond angle deviation from the predicted value has to be identified.

Concept Introduction:

VSEPR Theory:

The basis for this theory is the electron pair that is bonded electron present in either single or double bonds or lone pair electrons, present in the valence shell tends to repel each other which then tend to be in position in order to minimize the repulsions.

According to VSEPR theory, the geometry is predicted by the minimizing the repulsions between electron-pairs in the bonds and lone-pairs of electrons. The VSEPR theory is summarized in the given table as,

  Electron-pairlone-pairElectron-pairgeometryMolecularshape20LinearLinear30TrigonalplanarTrigonalplanar21TrigonalplanarBent40TetrahedralTetrahedral31TetrahedralPyramidal22TetrahedralVshape50TrigonalbipyramidalTrigonalbipyramidal41TrigonalbipyramidalSeesaw32TrigonalbipyramidalTshape23TrigonalbipyramidalLinear60OctahedralOctahedral51OctahedralSquarepyramidal42OctahedralSquareplanar

  • • Bond angle is the angle between two bonds of a molecule and it is determined based on the electron-domain geometry.
  • • Electro-domain geometry includes both bond pairs and lone pairs of central atom for determining the geometry of molecule.

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Students have asked these similar questions
Measure the C-C-C and C-C-H bond angles in the energy-minimized models of cis and trans isomers of cyclooctene. Compare these values with those predicted by VSEPR. In which isomer are deviations from VSEPR predictions greater?
Measure the C-C-C and C-C-H bond angles in the energy-minimized model of cyclohexene and compare them with those predicted by VSEPR. Explain any differences.
Measure the C=C-C bond angles in the energy-minimized models of the cis and trans isomers of 2,2,5,5-tetramethyl-3-hexene. In which case is the deviation from VSEPR predictions greater?
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