Textbook Question
Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.
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Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of BenzeneProblem 6d
Bruice 8th EditionCh. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of BenzeneProblem 6dChapter 9, Problem 6d
Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.
d. 
Verified step by step guidance1
Identify the species in question and determine if it has resonance structures. Resonance occurs when there are delocalized electrons, such as lone pairs, π-bonds, or charges, that can be redistributed across the molecule.
Draw all possible resonance contributors for the species. To do this, move electrons (using curved arrows) while ensuring that the octet rule is satisfied for second-row elements and that formal charges are minimized. Use MathML to represent the structures if needed.
Evaluate the stability of each resonance contributor. Contributors with a full octet on all atoms, minimal formal charges, and negative charges on more electronegative atoms are more stable and contribute more to the resonance hybrid.
Rank the resonance contributors in order of decreasing contribution to the resonance hybrid based on their stability. The most stable contributor will have the highest contribution, while less stable contributors will contribute less.
Draw the resonance hybrid by combining the resonance contributors. Use dashed lines to represent delocalized π-bonds and partial charges to indicate the distribution of charge across the molecule.
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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 same arrangement of atoms but differ in the placement of electrons. These structures help illustrate the delocalization of electrons within a molecule, which contributes to its stability and reactivity. The actual structure of the molecule is a resonance hybrid, a weighted average of all valid resonance forms.
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Drawing Resonance Structures
Resonance Hybrid
The resonance hybrid is the actual structure of a molecule that is represented as a combination of its resonance contributors. It reflects the delocalization of electrons across the molecule, resulting in bond lengths and angles that are intermediate between those predicted by individual resonance structures. The hybrid is more stable than any single resonance contributor due to this electron delocalization.
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Stability of Resonance Contributors
The stability of resonance contributors is determined by factors such as the octet rule, charge distribution, and the presence of formal charges. Contributors that have full octets, minimal formal charges, and charge separation are generally more stable and thus make a greater contribution to the resonance hybrid. Ranking these contributors helps predict the most significant forms that influence the molecule's properties.
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Related Practice
Textbook Question
Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.
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Textbook Question
a. Predict the relative bond lengths of the three carbon–oxygen bonds in the carbonate ion.
b. What is the charge on each oxygen?
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Textbook Question
Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.
b.
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Textbook Question
Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.
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Textbook Question
Which species in each pair is more stable?
d.
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