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Chapter 9: Problem 57

(a) What is the difference between a localized \(\pi\) bond and a delocalized one? (b) How can you determine whether a molecule or ion will exhibit delocalized \(\pi\) bonding? (c) Is the \(\pi\) bond in \(\mathrm{NO}_{2}^{-}\) localized or delocalized?

Short Answer

Expert verified
(a) A localized 蟺 bond is confined between two specific atoms, while a delocalized 蟺 bond has its electron density distributed across more than two atoms in the molecule or ion. (b) To determine if a molecule or ion will exhibit delocalized 蟺 bonding, check for the presence of resonance structures, conjugation, and aromatic rings. (c) The 蟺 bond in NO2鈦� is delocalized, as it has two resonance structures where the 蟺 bond is distributed across two oxygen atoms.

Step by step solution

01

Recall the definition of 蟺 bonds

蟺 bonds are formed by the sideways overlap of two p orbitals. This type of bond is found in molecules containing double or triple bonds, like alkenes and alkynes. They are responsible for the rigidity of molecules and their restricted rotation around the bond axis.
02

Differentiate between localized and delocalized 蟺 bonds

A localized 蟺 bond is when the electron density of the bond is confined between two specific atoms. In contrast, a delocalized 蟺 bond features electron density that is spread across more than two atoms in the molecule or ion. Delocalized 蟺 bonding systems typically offer added stability to the molecule or ion due to the distribution of the electron density.
03

Determine the presence of delocalized 蟺 bonding

There are a few factors that can help in determining whether a molecule or ion exhibits delocalized 蟺 bonding: 1. The presence of resonance structures: If a molecule or ion can be represented by more than one valid Lewis structure, which shows a different arrangement of electrons, it is indicative of delocalized 蟺 bonding. 2. Conjugation: Delocalized 蟺 bonding often occurs in molecules or ions with conjugation - alternating single and double bonds. 3. The presence of an aromatic ring: Aromatic rings, such as benzene, are characterized by a cyclic delocalized 蟺 bonding system.
04

Analyze the NO2鈦� ion

In order to determine if the 蟺 bond in the NO2鈦� ion is localized or delocalized, we first need to draw the Lewis structure of NO2鈦�: O \ N = O / O鈦� There are two resonance structures of NO2鈦�, where the two oxygen atoms are double-bonded to the nitrogen atom: O \ N = O (Structure 1) / O鈦� O \ N鈦� - O (Structure 2) / O These two resonance structures indicate that the 蟺 bond in NO2鈦� is delocalized, as there is no single location for the 蟺 bond and it is distributed across two oxygen atoms.
05

Conclusion

(a) A localized 蟺 bond is confined between two specific atoms, while a delocalized 蟺 bond has its electron density distributed across more than two atoms in the molecule or ion. (b) To determine if a molecule or ion will exhibit delocalized 蟺 bonding, check for the presence of resonance structures, conjugation, and aromatic rings. (c) The 蟺 bond in NO2鈦� is delocalized, as it has two resonance structures where the 蟺 bond is distributed across two oxygen atoms.

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Most popular questions from this chapter

The \(\mathrm{O}-\mathrm{H}\) bond lengths in the water molecule \(\left(\mathrm{H}_{2} \mathrm{O}\right)\) are \(0.96 \AA\), and the \(\mathrm{H}-\mathrm{O}-\mathrm{H}\) angle is \(104.5^{\circ}\). The dipole moment of the water molecule is \(1.85 \mathrm{D}\). (a) In what directions do the bond dipoles of the \(\mathrm{O}-\mathrm{H}\) bonds point? In what direction does the dipole moment vector of the water molecule point? (b) Calculate the magnitude of the bond dipole of the \(\mathrm{O}-\mathrm{H}\) bonds. (Note: You will need to use vector addition to do this.) (c) Compare your answer from part (b) to the dipole moments of the hydrogen halides (Table 8.3). Is your answer in accord with the relative electronegativity of oxygen?

Consider the \(\mathrm{H}_{2}{ }^{+}\) ion. (a) Sketch the molecular orbitals of the ion, and draw its energy-level diagram. (b) How many electrons are there in the \(\mathrm{H}_{2}{ }^{+}\) ion? (c) Draw the electron configuration of the ion in terms of its MOs. (d) What is the bond order in \(\mathrm{H}_{2}{ }^{+}\) ? (e) Suppose that the ion is excited by light so that an electron moves from a lower-energy to a higher-energy MO. Would you expect the excitedstate \(\mathrm{H}_{2}{ }^{+}\) ion to be stable or to fall apart? Explain.

(a) What is the probability of finding an electron on the internuclear axis if the electron occupies a \(\pi\) molecular orbital? (b) For a homonuclear diatomic molecule, what similarities and differences are there between the \(\pi_{2 p}\) MO made from the \(2 p_{x}\) atomic orbitals and the \(\pi_{2 p}\) MO made from the \(2 p_{y}\) atomic orbitals? (c) Why are the \(\pi_{2 p}\) MOs lower in energy than the \(\pi_{2 p}^{*}\) MOs?

The vertices of a tetrahedron correspond to four alternating corners of a cube. By using analytical geometry, demonstrate that the angle made by connecting two of the vertices to a point at the center of the cube is \(109.5^{\circ}\), the characteristic angle for tetrahedral molecules.

An \(\mathrm{AB}_{3}\) molecule is described as having a trigonalbipyramidal electron-domain geometry. How many nonbonding domains are on atom A? Explain.
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