   Chapter 23, Problem 116SCQ

Chapter
Section
Textbook Problem

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.

Interpretation Introduction

Interpretation:

The reason for why there is a high barrier to rotation arround a carbon–carbon double bond than carbon–carbon single bond has to be explained

Concept introduction:

In Orbital overlap model of bonding , two nuclei’s of two atoms are approach each other and overlap their atomic orbitals. As the overlapping the energy increases, the interaction decreases.

After some distance the minimum energy is reached and it corresponds to the bonding distance. The two atoms of nuclei begin to repel and energy increases.

There is a high barrier to rotation arround a carbon –carbon double bond than carbon-carbon single bond because higher energy require to break the pi-bond than the sigma bond.

Explanation

If the carbon-carbon attached with double bond, it contains one σ and one π bond.

The π bond is formed by the sideways overlapping of p-orbitals. And it is formed above or below the plane of two carbon atom, whereas σ-bond can be formed by the end to end overlapping of orbitals.

The breaking of π-bond requires 251 kJ/mol and σ-bond require 12.44 kj/mol.

Therefore, there is a high barrier to rotation arround a carbon–carbon double bond than carbon-carbon single bond because higher energy require to break the pi-bond than the sigma bond

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