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Ch.8 - Basic Concepts of Chemical Bonding
Chapter 8, Problem 92b

The following three Lewis structures can be drawn for N2O:
(b) The N—N bond length in N2O is 1.12 Å, slightly longer than a typical N ≡N bond; and the N— O bond length is 1.19 Å, slightly shorter than a typical N ═O bond (see Table 8.4). Based on these data, which resonance structure best represents N2O?

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1
Identify the possible resonance structures for N2O. These structures will involve different arrangements of single, double, and triple bonds between the nitrogen and oxygen atoms.
Consider the bond lengths given: N—N bond is 1.12 Å and N—O bond is 1.19 Å. Compare these lengths to typical bond lengths: a typical N≡N bond is shorter than 1.12 Å, and a typical N═O bond is longer than 1.19 Å.
Analyze each resonance structure to determine the type of bonds present between the atoms. For example, one structure might have a N≡N triple bond and a N—O single bond, while another might have a N═N double bond and a N═O double bond.
Evaluate which resonance structure aligns best with the given bond lengths. The structure with a N—N bond length slightly longer than a typical N≡N bond and a N—O bond length slightly shorter than a typical N═O bond is most representative.
Select the resonance structure that best matches the observed bond lengths, indicating the most accurate depiction of the electron distribution in N2O.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Lewis Structures

Lewis structures are diagrams that represent the bonding between atoms in a molecule and the lone pairs of electrons that may exist. They help visualize the arrangement of electrons and the connectivity of atoms, which is crucial for understanding molecular geometry and reactivity. In the case of N2O, multiple Lewis structures can be drawn to depict different resonance forms, each contributing to the overall electronic structure of the molecule.
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Resonance

Resonance refers to the concept that some molecules can be represented by two or more valid Lewis structures, known as resonance structures. These structures differ only in the arrangement of electrons, not in the arrangement of atoms. The actual structure of the molecule is a hybrid of these resonance forms, which helps explain properties such as bond lengths and strengths, as seen in the N—N and N—O bonds of N2O.
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Bond Lengths

Bond length is the average distance between the nuclei of two bonded atoms. It is influenced by the type of bond (single, double, triple) and the atoms involved. In N2O, the bond lengths of N—N and N—O provide insight into the nature of the bonding and the stability of the resonance structures, indicating that the actual bond lengths are intermediate between those of typical N≡N and N═O bonds.
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Related Practice
Textbook Question

The hypochlorite ion, ClO-, is the active ingredient in bleach. The perchlorate ion, ClO4-, is a main component of rocket propellants. Draw Lewis structures for both ions. (b) What is the formal charge of Cl in the perchlorate ion, assuming the Cl—O bonds are all single bonds?

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Textbook Question

The hypochlorite ion, ClO-, is the active ingredient in bleach. The perchlorate ion, ClO4-, is a main component of rocket propellants. Draw Lewis structures for both ions. (c) What is the oxidation number of Cl in the hypochlorite ion? (d) What is the oxidation number of Cl in the perchlorate ion, assuming the Cl—O bonds are all single bonds?

Textbook Question

The following three Lewis structures can be drawn for N2O:

(a) Using formal charges, which of these three resonance forms is likely to be the most important?

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Open Question
(a) The nitrate ion, NO3^-, has a trigonal planar structure with the N atom as the central atom. Draw the Lewis structure(s) for the nitrate ion.
Textbook Question

Ortho-Dichlorobenzene, C6H4Cl2, is obtained when two of the adjacent hydrogen atoms in benzene are replaced with Cl atoms. A skeleton of the molecule is shown here. (a) Complete a Lewis structure for the molecule using bonds and electron pairs as needed.

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Textbook Question

Ortho-Dichlorobenzene, C6H4Cl2, is obtained when two of the adjacent hydrogen atoms in benzene are replaced with Cl atoms. A skeleton of the molecule is shown here. (b) Are there any resonance structures for the molecule? If so, sketch them.

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