Textbook Question
Given the following Keq values, how much stronger of a base is acetate (CH3CO2-) than chloride (Cl⁻)?
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Ch. 4 - Acids and Bases: Electron Flow
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- 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 I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: 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 I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: 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: 9780137566471Not the one you use?Change textbook
Chapter 3, Problem 25a
An unknown acid (HA) has been identified as very strong. What does this tell you about the stability of the conjugate base, A⁻? Is it strong or weak? Is it reactive or unreactive?
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Understand the relationship between acid strength and conjugate base stability: A strong acid (HA) dissociates completely in water, meaning it donates its proton (H⁺) readily. This implies that its conjugate base (A⁻) must be very stable, as it does not readily reaccept the proton.
Recall the principle of conjugate acid-base pairs: The stronger the acid, the weaker its conjugate base. Since HA is identified as a very strong acid, its conjugate base (A⁻) is weak.
Analyze the reactivity of the conjugate base: A weak conjugate base is typically unreactive because it is stable and does not have a strong tendency to gain a proton or participate in other chemical reactions.
Consider the implications for chemical behavior: The stability of A⁻ means it is less likely to interfere in reactions or act as a nucleophile, making it unreactive in most contexts.
Summarize the findings: The conjugate base (A⁻) of a very strong acid (HA) is weak and unreactive due to its high stability.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Theory
Acid-base theory explains the behavior of acids and bases in terms of proton transfer. A strong acid, like the unknown acid HA, completely dissociates in solution, releasing protons (H⁺) and forming its conjugate base (A⁻). The strength of an acid is inversely related to the strength of its conjugate base; thus, a very strong acid indicates that its conjugate base is weak.
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02:49
The Lewis definition of acids and bases.
Conjugate Base Stability
The stability of a conjugate base is crucial in determining the strength of its corresponding acid. A stable conjugate base (A⁻) is less likely to re-accept a proton, making the acid stronger. Factors influencing stability include electronegativity, resonance, and inductive effects; a weak conjugate base typically has lower stability, which aligns with the strong nature of the original acid.
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04:31Stability of Conjugated Intermediates
Reactivity of Conjugate Bases
The reactivity of a conjugate base is often linked to its stability. A weak conjugate base, such as A⁻ from a strong acid, is generally unreactive because it does not readily accept protons. This unreactivity stems from its stability, meaning it is less likely to participate in further acid-base reactions, contrasting with strong conjugate bases that are more reactive.
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05:29Definition of Conjugation
Related Practice
Textbook Question
Design an acid–base extraction scheme to separate a mixture of the basic amine N,N-dimethylaniline and naphthalene.
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Textbook Question
Given the following Keq values, how much stronger of an acid is methanol (CH3OH) than acetylene (HC≡CH)?
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Textbook Question
Given the Keq values for the following acid–base reactions, identify the strongest acid and the strongest base.
(c)
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Textbook Question
An unknown base (B⁻) has been identified as very weak. What does this tell you about the strength of its conjugate acid, HB? Is it stable or unstable? Is it reactive or unreactive?
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Textbook Question
Given the Keq values for the following acid–base reactions, identify the strongest acid and the strongest base.
(b)
1112
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