Textbook Question
Determine whether the following pairs of structures are actually different compounds or simply resonance forms of the same compounds.
a.
b.
c.
d.
2
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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 41i-l
Determine whether the following pairs of structures are actually different compounds or simply resonance forms of the same compounds.
i. 
j. 
k. 
l. 
Verified step by step guidance1
Identify the connectivity of atoms in each pair of structures. If the connectivity is the same, they might be resonance forms; if different, they are distinct compounds.
Check the placement of electrons, particularly pi electrons and lone pairs, in each structure. Resonance forms will have the same arrangement of atoms but different electron placements.
Examine the formal charges on atoms in each structure. Resonance forms can have different formal charges on atoms, but the overall charge of the molecule must remain the same.
Look for any changes in hybridization or geometry of atoms between the structures. Resonance forms should not involve changes in hybridization or geometry.
Consider the possibility of tautomerism, which involves the transfer of protons and changes in connectivity, distinguishing it from resonance, which only involves electron movement.
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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 Lewis structures for the same molecule that depict the delocalization of electrons within the molecule. They are used to represent molecules where the electron distribution cannot be described by a single Lewis structure. Resonance structures differ only in the positions of electrons, not in the positions of atoms.
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Drawing Resonance Structures
Structural Isomers
Structural isomers are compounds with the same molecular formula but different connectivity of atoms. Unlike resonance structures, structural isomers have different physical and chemical properties because the atoms are connected in different ways, leading to distinct compounds.
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Electron Delocalization
Electron delocalization refers to the spreading of electron density across several atoms, which is a key feature in resonance. This concept helps explain the stability of molecules with conjugated systems, where electrons are shared over multiple bonds, reducing the overall energy of the molecule.
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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)
2
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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.
3
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Textbook Question
For each of the following structures,
1. Draw a Lewis structure; fill in any nonbonding electrons.
2. Calculate the formal charge on each atom other than hydrogen
d. [(CH3)3O]+
e. CH3NC
f. (CH3)4NBr
1
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Textbook Question
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)
1
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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)
2
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