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Chapter 9: Problem 67

(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

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(a) A localized π bond is a covalent bond formed by the overlapping of two adjacent p orbitals and is restricted to two specific atoms, while a delocalized π bond involves the overlapping of p orbitals on more than two atoms, decreasing overall energy and increasing stability. (b) To determine delocalized π bonding: identify atoms with available p orbitals, determine atom hybridizations, check for resonance structures, and inspect electron distribution. (c) In the nitrite ion (NO₂⁻), the π bond is delocalized as the π electrons are distributed across both oxygen atoms, and there are resonance structures that show the π bond alternating between the two oxygen atoms.

Step by step solution

01

(a) Difference between localized and delocalized π bonds

A localized π bond is a covalent bond formed by the overlapping of two adjacent p orbitals and is restricted to two specific atoms. This type of π bond is found in simple molecules like ethene (C₂H₄). A delocalized π bond, on the other hand, involves the overlapping of p orbitals on more than two atoms. The electrons in such bonds are effectively spread out over several atoms within the molecule, essentially lowering the overall energy and increasing the stability of the system. This is commonly seen in compounds like benzene (C₆H₆), where the π electrons are delocalized over all six carbon atoms.
02

(b) Determine delocalized π bonding in a molecule or ion

In order to identify if a molecule or ion exhibits delocalized π bonding, we can follow these steps: 1. Identify the atoms that have p orbitals available for π bonding. This typically includes carbon, nitrogen, and oxygen atoms. 2. Determine the hybridization of the atoms identified in step 1. Atoms that are sp² or sp hybridized can participate in delocalized π bonding. 3. Check for resonance structures. If a molecule or ion has multiple resonance structures, it is likely to have delocalized π bonding. 4. Inspect the electron distribution across the molecule or ion. If the π electrons are distributed across multiple atoms within the molecule, then the π bonding is delocalized.
03

(c) π bond in nitrite ion (NO₂⁻) - localized or delocalized?

We will now determine whether the π bond in NO₂⁻ is localized or delocalized by following the steps from part (b): 1. The nitrite ion, NO₂⁻, contains one nitrogen atom and two oxygen atoms, all of which have p orbitals available for π bonding. 2. The nitrogen atom in NO₂⁻ is sp² hybridized, while the oxygen atoms are sp³ hybridized. 3. NO₂⁻ has resonance structures in which the π bond alternates between the two oxygen atoms. 4. The π electrons in NO₂⁻ are delocalized across both oxygen atoms. Based on this analysis, the π bond in the nitrite ion, NO₂⁻, is delocalized.

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Most popular questions from this chapter

(a) What is the difference between hybrid orbitals and molecular orbitals? (b) How many electrons can be placed into each MO of a molecule? (c) Can antibonding molecular orbitals have electrons in them?

Propylene, \(\mathrm{C}_{3} \mathrm{H}_{6},\) is a gas that is used to form the important polymer called polypropylene. Its Lewis structure is (a) What is the total number of valence electrons in the propylene molecule? (b) How many valence electrons are used to make \(\sigma\) bonds in the molecule? (c) How many valence electrons are used to make \(\pi\) bonds in the molecule? (d) How many valence electrons remain in nonbonding pairs in the molecule? (e) What is the hybridization at each carbon atom in the molecule?

Draw sketches illustrating the overlap between the following orbitals on two atoms: (a) the \(2 s\) orbital on each atom, (b) the \(2 p_{z}\) orbital on each atom (assume both atoms are on the \(z\) -axis), \((\mathrm{c})\) the \(2 s\) orbital on one atom and the \(2 p_{z}\) orbital on the other atom.

(a) What does the term diamagnetism mean? (b) How does a diamagnetic substance respond to a magnetic field? (c) Which of the following ions would you expect to be diamagnetic: \(\mathrm{N}_{2}^{2-}, \mathrm{O}_{2}^{2-}, \mathrm{Be}_{2}^{2+}, \mathrm{C}_{2}^{-} ?\)

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