Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 1, Problem 1.26SP
  1. a. Draw the resonance forms for SO2 (bonded O—S—O).
  2. b. Draw the resonance forms for ozone (bonded O—O—O).
  3. c. Sulfur dioxide has one more resonance form than ozone Explain why this structure is not possible for ozone.

(a)

Expert Solution
Check Mark
Interpretation Introduction

To determine: The resonating structures of SO2 molecule.

Interpretation: The resonating structures of SO2 molecule are to be stated.

Concept introduction: Resonance is the process in which a molecule gets different structures to define its bonding within the molecule. Such molecules cannot be represented in single Lewis structures. Resonating structures of such molecules are called contributing structures. In the process of resonance, shifting of lone pairs occurs with the bonds and other lone pairs.

Answer to Problem 1.26SP

The resonating structures of SO2 molecule are shown in Figure 1.

Explanation of Solution

The resonating structures of the given molecule are shown as,

Organic Chemistry (9th Edition), Chapter 1, Problem 1.26SP , additional homework tip  1

Figure 1

The given compound is SO2. Sulfur is present at the centre of the molecule. Two oxygen atoms are arranged around carbon. In first structure, sulfur is present at the centre. It is bonded with two oxygen atoms by double bonds. In second structure, one oxygen atom carries a negative charge with three lone pairs and one oxygen atom carries only two lone pairs of electron. Third structure is same as second one. Only different oxygen are involved. Shifting and movement of electrons, bonds and charges take place to get resonating structures of SO2.

(b)

Expert Solution
Check Mark
Interpretation Introduction

To determine: The resonating structures of O3 molecule.

Interpretation: The resonating structures of O3 molecule are to be stated.

Concept introduction: Resonance is the process in which a molecule gets different structures to define its bonding within the molecule. Such molecules cannot be represented in single Lewis structures. Resonating structures of such molecules are called contributing structures. In the process of resonance, shifting of lone pairs occurs with the bonds and other lone pairs.

Answer to Problem 1.26SP

The resonating structures of the given molecule are shown in Figure 2.

Explanation of Solution

The resonating structures of the given molecule are shown as,

Organic Chemistry (9th Edition), Chapter 1, Problem 1.26SP , additional homework tip  2

Figure 2

The given compound is trioxygen. In this molecule, three oxygen atoms are joined together by one double and one single bond. One oxygen atom carries a positive charge and one carries a negative charge. The positive charge, negative charge and a double bond present in conjugation in the given molecule. It results in the resonating structures of O3 molecule.

(c)

Expert Solution
Check Mark
Interpretation Introduction

To determine: The reason corresponding to the fact that ozone has only two resonating structures, whereas sulfur dioxide has three.

Interpretation: The reason corresponding to the given fact is to be stated.

Concept introduction: Resonance is the process in which a molecule gets different structures to define its bonding within the molecule. Such molecules cannot be represented in single Lewis structures. Resonating structures of such molecules are called contributing structures. In the process of resonance, shifting of lone pairs occurs with the bonds and other lone pairs.

Answer to Problem 1.26SP

The reason corresponding to the given fact is stated below.

Explanation of Solution

Both the sulfur dioxide and ozone molecules are triatomic and both contain atoms of oxygen family. But the resonating structures of sulfur dioxide are more than ozone. The main reason for this is the difference in the group number of the central atom.

In sulfur dioxide, sulfur is present as a central atom, whereas in ozone oxygen atom is present as a central atom. Rest of the surrounding atoms in both the molecules are same. Atomic number of sulfur is sixteen. Whereas, oxygen has the atomic number eight. Therefore, sulfur contains third shell too and it is capable to handle extra bond by using empty “d” orbital and also able to show more resonating structures. This is not the case with ozone molecule. Hence, sulfur dioxide has more resonating structures than ozone molecule.

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Students have asked these similar questions
For resonance, there can be two resonance contributors or there could be one resonance hybrid. Are these just different ways to express the resonance? Do you have either two resonance contributors or a resonance hybrid? Or is the resonance hybrid just the resonance structure, but the version that is found in nature?
The curved arrow notation introduced in Section 1.6B is a powerful method used by organic chemists to show the movement of electrons not only in resonance structures, but also in chemical reactions.Because each curved arrow shows the movement of two electrons, following the curved arrows illustrates what bonds are broken and formed in a reaction. Consider the following three-step process. (a) Add curved arrows in Step [1] to show the movement of electrons. (b) Use the curved arrows drawn in Step [2] to identify the structure of X. X is converted in Step [3] to phenol and HCl.
a) what is the best resonance structure?

Chapter 1 Solutions

Organic Chemistry (9th Edition)

Ch. 1.10A - Draw complete Lewis structures for the following...Ch. 1.10B - Give Lewis structures corresponding to the...Ch. 1.10B - Prob. 1.13PCh. 1.11 - Compute the empirical and molecular formulas for...Ch. 1.16 - a. Use your molecular models to make ethane, and...Ch. 1.17 - a. Predict the hybridization of the oxygen atom in...Ch. 1.17 - Predict the hybridization geometry and bond angles...Ch. 1.17 - Predict the hybridization, geometry, and bond...Ch. 1.17 - Prob. 1.19PCh. 1.17 - Allene, CH2=C=CH2, has the structure shown below...Ch. 1.17 - 1. Draw the important resonance forms for each...Ch. 1.18B - Prob. 1.22PCh. 1.18B - Two compounds with the formula CH3CH=NCH3 are...Ch. 1.19B - Prob. 1.24PCh. 1.19B - Give the relationship between the following pairs...Ch. 1 - a. Draw the resonance forms for SO2 (bonded OSO)....Ch. 1 - Name the element that corresponds to each...Ch. 1 - Prob. 1.28SPCh. 1 - For each compound, state whether its bonding is...Ch. 1 - a. Both PCl3 and PCl5 are stable compounds Draw...Ch. 1 - Draw a Lewis structure for each species a. N2H4 b....Ch. 1 - Prob. 1.32SPCh. 1 - Prob. 1.33SPCh. 1 - Draw Lewis structures for a. two compounds of...Ch. 1 - Prob. 1.35SPCh. 1 - Some of the following molecular formulas...Ch. 1 - Prob. 1.37SPCh. 1 - Give the molecular formula of each compound shown...Ch. 1 - 1. From what you remember of electronegativities,...Ch. 1 - For each of the following structures, 1. Draw a...Ch. 1 - Prob. 1.41SPCh. 1 - Prob. 1.42SPCh. 1 - Prob. 1.43SPCh. 1 - Prob. 1.44SPCh. 1 - For each pair of ions, determine which on is more...Ch. 1 - Use resonance structures to identify the areas of...Ch. 1 - Prob. 1.47SPCh. 1 - In 1934, Edward A. Doisy of Washington University...Ch. 1 - If the carbon atom in CH2Cl2 were fat. there would...Ch. 1 - Cyclopropane (C3H6, a three-membered ring) is more...Ch. 1 - Prob. 1.51SPCh. 1 - Prob. 1.52SPCh. 1 - In most amines, the nitrogen atom is sp3...Ch. 1 - Predict the hybridization and geometry of the...Ch. 1 - Draw orbital pictures of the pi bonding in the...Ch. 1 - Prob. 1.56SPCh. 1 - Prob. 1.57SPCh. 1 - Which of the following compounds show cis-trans...Ch. 1 - Give the relationships between the following pairs...Ch. 1 - Dimethyl sulfoxide (DMSO) has been used as an...
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