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Chapter 9: Problem 63

(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) Localized π bonds are formed between two adjacent atoms and are restricted to the region between them, whereas delocalized π bonds involve overlapping of more than two atomic orbitals across three or more atoms. (b) To determine if a molecule or ion exhibits delocalized π bonding, look for resonance structures with π bonds shared across three or more atoms. (c) The π bond in the nitrite ion, \(\mathrm{NO}_{2}^{-}\), is delocalized.

Step by step solution

01

Explaining Localized and Delocalized π bonds

Localized π bonds are formed between two adjacent atoms and are restricted to the region between these two atoms. In contrast, delocalized π bonds involve the overlapping of more than two atomic orbitals across three or more atoms. This leads to an electron cloud that extends over multiple atoms, distributing the bonding electrons across a larger area.
02

Determination of Delocalized π bonds in a Molecule or Ion

To determine whether a molecule or ion exhibits delocalized π bonding, examine the structure of the compound and look for resonance structures. If there is more than one possible structure with π bonds, check whether these structures share electrons across three or more atoms. If the electrons are distributed over multiple atoms, this suggests delocalized π bonding.
03

Analyzing the π bond in the Nitrite Ion, \(\mathrm{NO}_{2}^{-}\)

The nitrite ion (\(\mathrm{NO}_{2}^{-}\)) has two resonance structures, as shown below: (1) O-N=O^(-) ↔ (2) O^(-)-N=O In these resonance structures, the π bond is distributed between the two oxygen atoms and the nitrogen atom. The electron cloud that forms the π bond is spread over three atoms, which indicates delocalized π bonding.
04

Answer

(a) Localized π bonds are formed between two adjacent atoms and are restricted to the region between them, whereas delocalized π bonds involve overlapping of more than two atomic orbitals across three or more atoms. (b) To determine if a molecule or ion exhibits delocalized π bonding, look for resonance structures with π bonds shared across three or more atoms. (c) The π bond in the nitrite ion, \(\mathrm{NO}_{2}^{-}\), is delocalized.

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Most popular questions from this chapter

Describe the bond angles to be found in each of the follow- ing molecular structures: (a) trigonal planar, \((\mathbf{b})\) tetrahedral, (c) octahedral, (d) linear.

Azo dyes are organic dyes that are used for many applications, such as the coloring of fabrics. Many azo dyes are derivatives of the organic substance azobenzene, \(\mathrm{C}_{12} \mathrm{H}_{10} \mathrm{~N}_{2}\) A closely related substance is hydrazobenzene, $\mathrm{C}_{12} \mathrm{H}_{12} \mathrm{~N}_{2}$ (Recall the shorthand notation used for benzene.) (a) What is the hybridization at the \(\mathrm{N}\) atom in each of the substances? (b) How many unhybridized atomic orbitals are there on the \(\mathrm{N}\) and the \(\mathrm{C}\) atoms in each of the substances? (c) Predict the \(\mathrm{N}-\mathrm{N}-\mathrm{C}\) angles in each of the substances. (d) Azobenzene is said to have greater delocalization of its \(\pi\) electrons than hydrazobenzene. Discuss this statement in light of your answers to (a) and (b). (e) All the atoms of azobenzene lie in one plane, whereas those of hydrazobenzene do not. Is this observation consistent with the statement in part (d)? (f) Azobenzene is an intense red-orange color, whereas hydrazobenzene is nearly colorless. Which molecule would be a better one to use in a solar energy conversion device? (See the "Chemistry Put to Work" box for more information about solar cells.)

Give the electron-domain and molecular geometries of a molecule that has the following electron domains on its central atom: (a) four bonding domains and no nonbonding domains, (b) three bonding domains and two nonbonding domains, (c) five bonding domains and one nonbonding domain, (d) four bonding domains and two nonbonding domains.

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