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

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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1
Identify the three possible Lewis structures for N2O. Each structure should have a different arrangement of single, double, or triple bonds between the nitrogen and oxygen atoms.
Calculate the formal charge for each atom in each of the three Lewis structures. The formal charge can be calculated using the formula: \( \text{Formal Charge} = \text{Valence Electrons} - \text{Non-bonding Electrons} - \frac{1}{2} \times \text{Bonding Electrons} \).
Compare the formal charges across the three structures. The most stable structure typically has the smallest formal charges on each atom, ideally as close to zero as possible.
Consider the electronegativity of the atoms involved. Oxygen is more electronegative than nitrogen, so it is preferable for oxygen to have a negative formal charge if any atom must have one.
Select the resonance structure with the most favorable formal charges and distribution, taking into account both the magnitude of the charges and the electronegativity of the atoms.

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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 use dots to represent valence electrons and lines to represent bonds. Understanding how to draw and interpret Lewis structures is essential for visualizing molecular geometry and predicting reactivity.
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Formal Charge

Formal charge is a theoretical charge assigned to an atom in a molecule, calculated based on the number of valence electrons, the number of bonds, and the number of lone electrons. It helps in determining the most stable resonance structure by minimizing the formal charges across the molecule. A lower formal charge on atoms generally indicates a more stable structure.
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Resonance Structures

Resonance structures are different Lewis structures that represent the same molecule, differing only in the arrangement of electrons. They illustrate the delocalization of electrons within a molecule, which can affect its stability and reactivity. The true structure of the molecule is a hybrid of these resonance forms, and the most significant contributors are those with the lowest formal charges.
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Related Practice
Textbook Question

A major challenge in implementing the 'hydrogen economy' is finding a safe, lightweight, and compact way of storing hydrogen for use as a fuel. The hydrides of light metals are attractive for hydrogen storage because they can store a high weight percentage of hydrogen in a small volume. For example, NaAlH4 can release 5.6% of its mass as H2 upon decomposing to NaH(s), Al(s), and H2(g). NaAlH4 possesses both covalent bonds, which hold polyatomic anions together, and ionic bonds. (d) What is the formal charge on hydrogen in the polyatomic ion?

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Textbook Question

Although I3- is a known ion, F3- is not. (c) Another classmate says F3- does not exist because it would violate the octet rule. Is this classmate possibly correct?

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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. (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 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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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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