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Ch.8 - Basic Concepts of Chemical Bonding
Chapter 8, Problem 95a

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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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

Structures A, B, and C show the connectivity of the atoms in three different molecules that are isomers of C3H4O. By completing the Lewis structures of these molecules, complete the information in the following table:

Isomer A Isomer B Isomer C

Number of single bonds

Number of double bonds

Number of triple bonds

Number of nonbonding pairs

Textbook Question

The triiodide ion, I3-, exists, whereas the corresponding ion with fluorine, F3-, does not. The I3- ion has a linear structure in which two outer I atoms are each bonded to a central I atom. Although I3- is a known ion, F3- is not.

c. Which of the following statements about the existence of I3- versus the nonexistence of F3- is or are true?

i. The Lewis structure of I3- shows 12 electrons around the central I atom.

ii. Elements from the second row of the periodic table generally do not form hypervalent molecules and ions.

iii. An I atom can form a hypervalent molecule or ion more readily than an F atom because of the larger size of the I atom.


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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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Textbook Question

Mothballs are composed of naphthalene, C10H8, a molecule that consists of two six-membered rings of carbon fused along an edge, as shown in this incomplete Lewis structure:(a) Draw all of the resonance structures of naphthalene. How many are there?

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Textbook Question

Mothballs are composed of naphthalene, C10H8, a molecule that consists of two six-membered rings of carbon fused along an edge, as shown in this incomplete Lewis structure:

(b) Do you expect the C—C bond lengths in the molecule to be similar to those of C—C single bonds, C ═ C double bonds, or intermediate between C—C single and C ═ C double bonds?

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