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.
c.
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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 6e
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 6eChapter 9, Problem 6e
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.
e. 
Verified step by step guidance1
Step 1: Identify the resonance contributors by analyzing the structure. The molecule contains a positively charged oxygen atom, a carbonyl group, and an amine group with a lone pair of electrons. Resonance contributors will involve the delocalization of electrons from the lone pair on the nitrogen and the π-electrons of the carbonyl group.
Step 2: Draw the first resonance structure. Move the lone pair of electrons from the nitrogen to form a double bond between the nitrogen and the carbon. Simultaneously, move the π-electrons of the carbonyl group to the oxygen atom, neutralizing the positive charge on oxygen.
Step 3: Draw the second resonance structure. Move the lone pair of electrons from the oxygen atom back to form a double bond between the oxygen and the carbon. Simultaneously, break the double bond between the nitrogen and the carbon, returning the lone pair to the nitrogen.
Step 4: Rank the resonance contributors based on their stability. The most stable contributor will have the least separation of charges and obey the octet rule for all atoms. Contributors with a neutral oxygen atom and delocalized charges are generally more stable.
Step 5: Draw the resonance hybrid. Combine the resonance contributors into a single structure that represents the delocalization of electrons. Use dashed lines to indicate partial bonds and partial charges to show the distribution of electron density 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 distribution of electrons. These structures help illustrate the delocalization of electrons within a molecule, which contributes to its overall stability. The actual structure of the molecule is a resonance hybrid, a weighted average of all valid resonance forms.
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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, leading to increased stability. The hybrid structure often has bond lengths and angles that are intermediate between those predicted by the individual resonance forms, providing a more accurate depiction of the molecule's electronic structure.
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Electronegativity and Charge Distribution
Electronegativity refers to the tendency of an atom to attract electrons towards itself. In resonance structures, the distribution of charges is influenced by the electronegativity of the atoms involved. For example, in the given species with OH and NH2 groups, the resonance contributors will vary based on how the positive and negative charges are stabilized by the electronegative atoms, affecting the overall contribution of each resonance form to the hybrid.
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Related Practice
Textbook Question
List the following in order of decreasing delocalization energy:
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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.
f.
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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.
d.
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