Domanda del libro di testo
When a secondary haloalkane is treated with sodium ethoxide in ethanol, we predict alkene formation over ether formation. How did we make this determination?
1991
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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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TOC.tableOfContents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases/Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Non è quello che usi tu?Cambia libro di testo
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Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 17
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 17Capitolo 12, Problema 17
Rationalize the difference in pKₐ values for the two hydroxyl groups.
Guida verificata passo dopo passo1
Identify the two hydroxyl groups in the molecule: one is attached directly to the benzene ring (phenol group), and the other is part of an alcohol group attached to the benzyl position.
Recall that the pKₐ value is a measure of the acidity of a compound. A lower pKₐ indicates a stronger acid, meaning the proton is more easily donated.
Analyze the phenol group (pKₐ = 10): The hydroxyl group attached to the benzene ring is more acidic due to resonance stabilization. When the proton is lost, the resulting phenoxide ion is stabilized by delocalization of the negative charge across the aromatic ring.
Analyze the alcohol group (pKₐ = 16): The hydroxyl group attached to the benzyl position is less acidic because the conjugate base (alkoxide ion) does not benefit from resonance stabilization. The negative charge remains localized on the oxygen atom, making it less stable.
Compare the two groups: The difference in pKₐ values arises from the resonance stabilization of the phenoxide ion in the phenol group, which makes it easier to lose a proton compared to the alcohol group, where no such stabilization occurs.
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Acidity and pKa
pKa is a quantitative measure of the strength of an acid in solution, representing the negative logarithm of the acid dissociation constant (Ka). A lower pKa value indicates a stronger acid, meaning it dissociates more readily in solution. Understanding pKa is essential for comparing the acidity of different functional groups, such as hydroxyl groups in this case.
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07:45
Identifying pKa values
Hydroxyl Groups
Hydroxyl groups (-OH) are functional groups that can influence the acidity of a compound. The position of the hydroxyl group relative to other substituents in a molecule can affect its ability to donate a proton, thus altering its pKa. Factors such as electronegativity and steric hindrance play significant roles in determining the acidity of hydroxyl groups.
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04:42Sequence Groups
Resonance and Inductive Effects
Resonance and inductive effects are key factors that can stabilize or destabilize the conjugate base formed after deprotonation of an acid. Resonance allows for the delocalization of negative charge, which can enhance stability and lower pKa. Inductive effects, caused by electronegative atoms or groups nearby, can either withdraw or donate electron density, further influencing the acidity of hydroxyl groups.
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01:47Understanding the Inductive Effect.
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