Can sigma bonds break?

Sigma bonds are never broken or made, because of this atoms must maintain their same position.

chem.libretexts.org - 1.7: Rules for Resonance Forms - Chemistry LibreTexts

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Recognizing resonance

Resonance contributors involve the ‘imaginary movement’ of pi-bonded electrons or of lone-pair electrons that are adjacent to (i.e. conjugated to) pi bonds. You can never shift the location of electrons in sigma bonds – if you show a sigma bond forming or breaking, you are showing a chemical reaction taking place. Likewise, the positions of atoms in the molecule cannot change between two resonance contributors. Because benzene will appear throughout this course, it is important to recognize the stability gained through the resonance delocalization of the six pi electrons throughout the six carbon atoms. Benzene also illustrates one way to recognize resonance - when it is possible to draw two or more equivalent Lewis structures. If we were to draw the structure of an aromatic molecule such as 1,2-dimethylbenzene, there are two ways that we could draw the double bonds: Which way is correct? There are two simple answers to this question: 'both' and 'neither one'. Both ways of drawing the molecule are equally acceptable approximations of the bonding picture for the molecule, but neither one, by itself, is an accurate picture of the delocalized pi bonds. The two alternative drawings, however, when considered together, give a much more accurate picture than either one on its own. This is because they imply, together, that the carbon-carbon bonds are not double bonds, not single bonds, but about halfway in between. When it is possible to draw more than one valid structure for a compound or ion, we have identified resonance contributors: two or more different Lewis structures depicting the same molecule or ion that, when considered together, do a better job of approximating delocalized pi-bonding than any single structure. By convention, resonance contributors are linked by a double-headed arrow, and are sometimes enclosed by brackets: In order to make it easier to visualize the difference between two resonance contributors, small, curved arrows are often used. Each of these arrows depicts the ‘movement’ of two pi electrons. In the drawing of resonance contributors, however, this electron ‘movement’ occurs only in our minds, as we try to visualize delocalized pi bonds. Nevertheless, use of the curved arrow notation is an essential skill that you will need to develop in drawing resonance contributors. The depiction of benzene using the two resonance contributors A and B in the figure above does not imply that the molecule at one moment looks like structure A, then at the next moment shifts to look like structure B. Rather, at all moments, the molecule is a combination, or resonance hybrid of both A and B. Caution! It is very important to be clear that in drawing two (or more) resonance contributors, we are not drawing two different molecules: they are simply different depictions of the exact same molecule. Furthermore, the double-headed resonance arrow does NOT mean that a chemical reaction has taken place. Benzene is often drawn as only one of the two possible resonance contributors (it is assumed that the reader understands that resonance hybridization is implied). However, sometimes benzene will be drawn with a circle inside the hexagon, either solid or dashed, as a way of drawing a resonance hybrid.

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Are sigma or pi bonds harder to break?

Pi bonds are easier to break than sigma bonds. There are two reasons for this. The end-on overlap of orbitals to form a sigma bond is more efficient than the side-on overlap of orbitals to form a pi bond.

socratic.org - Are pi bonds easier to break? | Socratic

Pi bonds are easier to break than sigma bonds.

There are two reasons for this.

Overlap efficiency

The end-on overlap of orbitals to form a sigma bond is more efficient than the side-on overlap of orbitals to form a pi bond.

Distance from the nuclei

The electrons in a sigma bond are directly between the two nuclei. They are as close to the nuclei as they can get. The nuclei have a strong hold on the electrons, so it is difficult to break a sigma bond. The electrons in a pi bond are further away from the nuclei. The nuclei have a weaker attraction to the electrons, so it is easier to break a pi bond.

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