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 4c
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 4cChapter 9, Problem 4c
Which species in each pair is more stable?
c. 
Verified step by step guidance1
Analyze the structures of the two species provided. Both species contain an oxygen atom with a negative charge (-O⁻) attached to a carbon chain. The difference lies in the substitution pattern of the alkene group.
Consider the concept of alkene stability. Alkenes are stabilized by hyperconjugation and inductive effects from alkyl groups attached to the double bond. More substituted alkenes are generally more stable due to increased hyperconjugation.
Examine the first species (CH₃CHCH=CH₂). The double bond is monosubstituted, meaning it has only one alkyl group (CH₃) attached to the double bond. This results in lower stability compared to more substituted alkenes.
Examine the second species (CH₃C=CHCH₃). The double bond is disubstituted, meaning it has two alkyl groups (CH₃ and CH₃) attached to the double bond. This increases stability due to greater hyperconjugation and inductive effects.
Conclude that the second species (CH₃C=CHCH₃) is more stable than the first species (CH₃CHCH=CH₂) because the double bond in the second species is more substituted, leading to increased stabilization.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Stability of Chemical Species
The stability of chemical species refers to their tendency to maintain their structure and resist change. Factors influencing stability include the energy of the species, resonance structures, and steric hindrance. More stable species typically have lower energy and are less reactive, making them less likely to undergo chemical transformations.
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Resonance Structures
Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. A molecule with multiple resonance forms can distribute its electron density more evenly, leading to increased stability. The actual structure of the molecule is a hybrid of these forms, and the more resonance forms a species has, the more stable it generally is.
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Steric Hindrance
Steric hindrance occurs when atoms within a molecule are forced into close proximity, leading to repulsive interactions that can destabilize the structure. Larger groups or substituents can create steric strain, making a molecule less stable. Understanding steric effects is crucial for predicting the stability of different species, especially in organic compounds.
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Related Practice
Textbook Question
Between 1865 and 1890, other possible structures were proposed for benzene, such as those shown here. Considering what nineteenth-century chemists knew about benzene, which is a better proposal for benzene’s structure: Dewar benzene or Ladenburg benzene? Why?
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Textbook Question
Which species in each pair is more stable?
a.
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Textbook Question
Which species in each pair is more stable?
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.
b.
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Textbook Question
Which species in each pair is more stable?
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