Textbook Question
For each of these ions, draw the important resonance forms and predict which resonance form is likely to be the major contributor.
(c)
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Ch.1 - Structure and Bonding
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 1, Problem 43d,e
In the following sets of resonance forms, label the major and minor contributors and state which structures would be of equal energy. Add any missing important resonance forms.
(d) 
(e) 
Verified step by step guidance1
Identify the resonance structures in each set. For set (d), the structures involve a nitro group and a carbanion. For set (e), the structures involve an amine group and a carbocation.
Evaluate the stability of each resonance structure. In set (d), the carbanion is more stable when it is adjacent to the electron-withdrawing nitro group, making it a major contributor. In set (e), the resonance structure with the positive charge on the more substituted carbon is more stable.
Determine the major and minor contributors. In set (d), the structure with the carbanion next to the nitro group is the major contributor. In set (e), the structure with the positive charge on the more substituted carbon is the major contributor.
Check for any missing resonance forms. In set (d), consider if there are any other possible resonance forms involving the movement of electrons. In set (e), consider if there are any other possible resonance forms involving the movement of electrons.
State which structures would be of equal energy. In set (d), the two structures are not of equal energy due to the differing stability of the carbanion positions. In set (e), the two structures are not of equal energy due to the differing stability of the carbocation positions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Resonance Structures
Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. They help in understanding the actual electronic structure of a molecule, which is a hybrid of all possible resonance forms. The stability and contribution of each resonance form depend on factors like the octet rule, charge distribution, and the presence of electronegative atoms.
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Major and Minor Contributors
In resonance theory, major contributors are the resonance forms that are more stable and thus have a greater influence on the overall structure of the molecule. Minor contributors are less stable forms that contribute less to the resonance hybrid. Factors such as formal charge, octet fulfillment, and the presence of electronegative atoms determine the stability of these contributors.
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Equal Energy Structures
Equal energy structures refer to resonance forms that have the same energy level and thus contribute equally to the resonance hybrid. These forms typically have similar stability and do not favor one over the other. Identifying these structures is crucial for understanding the reactivity and properties of the molecule, as they can influence the distribution of electron density.
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Related Practice
Textbook Question
Draw the important resonance forms to show the delocalization of charges in the following ions. In each case, indicate the major resonance form(s).
(j)
(k)
2139
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Textbook Question
Determine whether the following pairs of structures are actually different compounds or simply resonance forms of the same compounds.
e.
f.
g.
h.
1564
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1
rank
Textbook Question
For each of these ions, draw the important resonance forms and predict which resonance form is likely to be the major contributor.
(a)
695
views
Textbook Question
Determine whether the following pairs of structures are actually different compounds or simply resonance forms of the same compounds.
i.
j.
k.
l.
970
views
Textbook Question
For each of these ions, draw the important resonance forms and predict which resonance form is likely to be the major contributor.
(b)
664
views