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

Consider the hypothetical molecule B-A=B. Are the following statements true or false? (a) This molecule cannot exist. (b) If resonance was important, the molecule would have identical A–B bond lengths.

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insert step 1> Identify the type of bonds present in the molecule B-A=B. The molecule has a single bond (A-B) and a double bond (A=B).
insert step 2> Consider the possibility of the molecule's existence. For statement (a), evaluate if the molecule can exist based on the stability of the bonds and the elements involved.
insert step 3> For statement (b), consider the concept of resonance. Resonance occurs when there are multiple valid Lewis structures for a molecule. Determine if resonance is possible for B-A=B and how it would affect bond lengths.
insert step 4> Analyze the bond lengths in the context of resonance. If resonance is significant, the bond lengths between A and B would be averaged, leading to identical bond lengths.
insert step 5> Conclude the truthfulness of each statement based on your analysis of the molecule's structure and resonance possibilities.

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Key Concepts

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

Resonance

Resonance is a concept in chemistry that describes the delocalization of electrons in molecules where the bonding cannot be expressed by a single Lewis structure. Instead, multiple structures, known as resonance structures, contribute to the overall hybrid structure of the molecule. This delocalization can affect bond lengths and stability, leading to properties that differ from those predicted by any single structure.
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Bond Lengths

Bond length refers to the average distance between the nuclei of two bonded atoms. In molecules with resonance, the bond lengths can be equalized due to the sharing of electron density across multiple structures. For example, in resonance-stabilized molecules, bonds may exhibit lengths that are intermediate between single and double bonds, reflecting the influence of resonance on molecular geometry.
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Molecular Stability

Molecular stability is determined by the energy of a molecule, which is influenced by factors such as bond strength, electron delocalization, and steric interactions. Molecules that can delocalize electrons through resonance are often more stable than those that cannot, as the energy is lowered by the distribution of electron density. Understanding stability helps predict whether a hypothetical molecule can exist under normal conditions.
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Related Practice
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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Textbook Question

An important reaction for the conversion of natural gas to other useful hydrocarbons is the conversion of methane to ethane. 2 CH4(g) → C2H6(g) + H2(g) In practice, this reaction is carried out in the presence of oxygen, which converts the hydrogen produced into water. 2 CH4(g) + 12 O2(g) → C2H6(g) + H2O(g) Use Table 8.3 to estimate H for these two reactions. Why is the conversion of methane to ethane more favorable when oxygen is used? Why is the conversion of methane to ethane more favorable when oxygen is used?

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Textbook Question

Two compounds are isomers if they have the same chemical formula but different arrangements of atoms. Use Table 8.3 to estimate H for each of the following gas-phase isomerization reactions and indicate which isomer has the lower enthalpy. (d) Methyl isocyanide → Acetonitrile

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Textbook Question

The Ti2+ ion is isoelectronic with the Ca atom. (c) What charge would Ti have to be isoelectronic with Ca2+ ?

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