We can write two resonance structures for toluene, C6 H3 CH3: How would you expect the carbon-ca

Name: Problem 54, Chapter 7: Chemistry
Uploaded: 2021-09-18T10:15:44-08:00
Duration: 1 min 16 s
Channel: Harshit Mawandia
Description: We can write two resonance structures for toluene, C6 H3 CH3: How would you expect the carbon-carbon bond lengths in the six-membered ring of toluene to compare with the carbon-carbon bond length between the CH3 group and the carbon atom on the ring?

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Question

We can write two resonance structures for toluene, $\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CH}_{3}:$ How would you expect the carbon-carbon bond lengths in the six-membered ring of toluene to compare with the carbon-carbon bond length between the $\mathrm{CH}_{3}$ group and the carbon atom on the ring?

    We can write two resonance structures for toluene, $\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CH}_{3}:$ 
How would you expect the carbon-carbon bond lengths in the six-membered ring of toluene to compare with the carbon-carbon bond length between the $\mathrm{CH}_{3}$ group and the carbon atom on the ring?

Chemistry

Kenneth W Whitten 8th Edition

Chapter 7, Problem 54

Instant Answer

Solved by Expert Harshit Mawandia

09/18/2021

Step 1

Bond order is the number of chemical bonds between a pair of atoms. In toluene, the six-membered ring has a bond order of 1.5 due to the resonance structures, while the bond between the CH3 group and the carbon atom on the ring has a bond order of 1. Show more…

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We can write two resonance structures for toluene, $\mathrm{C}_{6} \mathrm{H}_{3} \mathrm{CH}_{3}:$ How would you expect the carbon-carbon bond lengths in the six-membered ring of toluene to compare with the carbon-carbon bond length between the $\mathrm{CH}_{3}$ group and the carbon atom on the ring?

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Key Concepts

Bond Order and Bond Length Relationship

The bond order, which is influenced by the degree of electron sharing between two bonded atoms, directly affects bond length. In aromatic rings, the bond order is intermediate between a single and a double bond due to partial double bond character from resonance. Consequently, these bonds become shorter and more uniform compared to typical single bonds, such as the bond between the CH? group and the aromatic ring carbon, which lacks the delocalized ? electron contribution and is usually longer.

Resonance in Aromatic Systems

Resonance in aromatic systems involves multiple contributing structures that share the delocalization of electrons around a cyclic ring. In an aromatic ring like that in toluene, the electrons are delocalized over the entire ring, leading to equalization of the bond lengths. This concept is central to understanding the stability and uniformity of electronic distribution in aromatic compounds.

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