Question

There is a high barrier to rotation around a carbon-carbon double bond, whereas the barrier to rotation around a carbon-carbon single bond is considerably smaller. Use the orbital overlap model of bonding (Chapter 9 ) to explain why there is restricted rotation around a double bond.

Name: Problem 116, Chapter 23: Chemistry and Chemical Reactivity
Uploaded: 2023-03-08T19:13:43-08:00
Channel: Tom Comey
Description: There is a high barrier to rotation around a carbon-carbon double bond, whereas the barrier to rotation around a carbon-carbon single bond is considerably smaller. Use the orbital overlap model of bonding (Chapter 9 ) to explain why there is restricted rotation around a double bond.

   There is a high barrier to rotation around a carbon-carbon double bond, whereas the barrier to rotation around a carbon-carbon single bond is considerably smaller. Use the orbital overlap model of bonding (Chapter 9 ) to explain why there is restricted rotation around a double bond.

Chemistry and Chemical Reactivity

John C. Kotz, Paul… 10th Edition

Chapter 23, Problem 116

Instant Answer

Solved by Expert Tom Comey

03/08/2023

Step 1

This overlap forms a sigma bond, which is symmetrical about the bond axis. This allows for free rotation around the bond axis, as the overlap of the orbitals is maintained regardless of the orientation of the atoms. Show more…

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There is a high barrier to rotation around a carbon-carbon double bond, whereas the barrier to rotation around a carbon-carbon single bond is considerably smaller. Use the orbital overlap model of bonding (Chapter 9 ) to explain why there is restricted rotation around a double bond.

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Key Concepts

Sigma and Pi Bonds

A carbon-carbon double bond consists of two types of bonds: a sigma bond resulting from head-on orbital overlap and a pi bond from the lateral overlap of p orbitals. The sigma bond is generally robust and less affected by rotation, whereas the pi bond is highly sensitive to the relative orientation of the orbitals.

Orbital Overlap Model

This model explains the formation of chemical bonds through the overlap of atomic orbitals. The effectiveness of this overlap directly influences the strength of the resulting bond, as well as the spatial arrangement and orientation of the bond.

Restricted Rotation

The restricted rotation around a double bond is due to the presence of the pi bond. Rotation disrupts the optimal lateral overlap required for pi bonding, leading to a significant energy barrier that prevents free rotation, unlike the more flexible sigma bond.

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