Which of the following statements about benzene, C6H6, is or are true?
i. Benzene has two equivalent resonance structures.
ii. There are no nonbonding pairs in the Lewis structure for benzene.
iii. Benzene has three short and three long C—C bonds.

검증된 단계별 안내

Identify the molecular structure of benzene, \( \text{C}_6\text{H}_6 \), which is a planar ring with alternating double and single bonds.

Understand that benzene is best represented by resonance structures, which are two equivalent structures where the double bonds are in different positions.

Recognize that in the resonance hybrid of benzene, all C—C bonds are of equal length due to the delocalization of electrons, contradicting statement iii.

Examine the Lewis structure of benzene to confirm that there are no nonbonding electron pairs on the carbon atoms, supporting statement ii.

Conclude that statements i and ii are true, while statement iii is false, based on the equal bond lengths in benzene.

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주요 개념

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Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. In the case of benzene, C6H6, it has multiple resonance structures that contribute to its overall stability. However, these structures are not equivalent in terms of energy; rather, they represent the same molecule's electron distribution, leading to the concept of resonance hybrid.

Lewis Structure

A Lewis structure is a diagram that represents the bonding between atoms in a molecule and the lone pairs of electrons that may exist. For benzene, the Lewis structure shows alternating single and double bonds between carbon atoms, but it is important to note that there are no nonbonding pairs of electrons on the carbon atoms, as all valence electrons are involved in bonding.

Bond Lengths in Benzene

Benzene exhibits a unique bonding situation where all carbon-carbon bonds are of equal length due to resonance. This results in bond lengths that are intermediate between single (C—C) and double (C=C) bonds, leading to the conclusion that benzene has six equivalent C—C bonds, rather than three short and three long bonds. This equal bond length is a key characteristic of aromatic compounds.

Which of the following statements about benzene, C6H6, is or are true?i. Benzene has two equivalent resonance structures.ii. There are no nonbonding pairs in the Lewis structure for benzene.iii. Benzene has three short and three long C—C bonds.