Domanda del libro di testo
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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TOC.tableOfContents
- 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
Capitolo 1, Problema 44b
For each of these ions, draw the important resonance forms and predict which resonance form is likely to be the major contributor.
(b) 
Guida verificata passo dopo passo1
Identify the ion in the structure: The given structure is a benzyl anion, where the negative charge is located on the CH2 group attached to the benzene ring.
Draw the first resonance structure: Move the lone pair of electrons from the negatively charged carbon to form a double bond with the adjacent carbon atom in the benzene ring. This will push the electrons in the adjacent double bond towards the next carbon atom, creating a new resonance structure.
Draw the second resonance structure: Continue the electron movement by pushing the electrons from the newly formed double bond to the next carbon-carbon double bond in the benzene ring, creating another resonance structure with the negative charge now on a different carbon atom in the ring.
Draw the third resonance structure: Repeat the electron movement process to push the electrons from the current double bond to the next carbon-carbon double bond, resulting in a resonance structure with the negative charge on yet another carbon atom in the benzene ring.
Predict the major contributor: Evaluate the resonance structures based on stability. The major contributor is typically the one where the negative charge is on the most electronegative atom or the one that maintains aromaticity. In this case, the structure that maintains the aromaticity of the benzene ring and has the negative charge on the CH2 group is likely the major contributor.
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Resonance Structures
Resonance structures are different Lewis structures for a molecule that depict the same arrangement of atoms but differ in the distribution of electrons. They are used to represent delocalized electrons within certain molecules where the bonding cannot be expressed by a single Lewis structure. The true structure is a hybrid of all possible resonance forms, contributing to the molecule's stability.
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Drawing Resonance Structures
Major Resonance Contributor
The major resonance contributor is the resonance structure that most accurately represents the molecule's electron distribution. It typically has the lowest energy, which is achieved by minimizing formal charges, maximizing covalent bonds, and placing negative charges on more electronegative atoms. This structure contributes most to the resonance hybrid, influencing the molecule's properties.
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Electronegativity and Charge Distribution
Electronegativity is the tendency of an atom to attract electrons towards itself. In resonance structures, the distribution of charges is influenced by electronegativity, with negative charges preferably residing on more electronegative atoms like oxygen. This affects the stability of resonance forms, as structures with charges on appropriate atoms are more stable and likely to be major contributors.
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1:47Electronegativity
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