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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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 24
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?
Verified step by step guidance1
Step 1: Recall the relationship between the strength of a base and its conjugate acid. A very weak base corresponds to a very strong conjugate acid. This is because the ability of the base to accept a proton is inversely related to the ability of its conjugate acid to donate a proton.
Step 2: Analyze the stability of the conjugate acid (HB). Strong acids tend to be stable because they readily donate protons and form stable conjugate bases. Therefore, if the base (B⁻) is very weak, its conjugate acid (HB) is likely stable.
Step 3: Consider the reactivity of the conjugate acid (HB). Strong acids are highly reactive because they easily donate protons in chemical reactions. Since HB is a strong acid, it is expected to be reactive.
Step 4: Summarize the findings: A very weak base (B⁻) indicates that its conjugate acid (HB) is strong, stable, and reactive.
Step 5: Apply this concept to other acid-base pairs to understand how the strength of a base influences the properties of its conjugate acid in various chemical contexts.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Conjugate Acid-Base Relationship
In acid-base chemistry, a conjugate acid is formed when a base accepts a proton (H⁺). The strength of a base is inversely related to the strength of its conjugate acid; thus, if a base is very weak, its conjugate acid is likely to be strong. This relationship is fundamental in predicting the behavior of acids and bases in chemical reactions.
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02:11
Equilibrium constant and conjugates.
Stability of Conjugate Acids
The stability of a conjugate acid is influenced by its ability to stabilize the positive charge that results from protonation. A weak base typically forms a stable conjugate acid because the conjugate acid does not readily donate the proton back, indicating that it is less reactive. Stability often correlates with the presence of electronegative atoms or resonance structures that can delocalize charge.
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Reactivity of Acids and Bases
Reactivity in acid-base chemistry refers to how readily an acid donates protons or a base accepts them. A weak base, such as B⁻, suggests that its conjugate acid, HB, is unreactive, as it does not easily release protons. This unreactivity is a characteristic of stable conjugate acids, which do not participate in further acid-base reactions under standard conditions.
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Related Practice
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)
1003
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Textbook Question
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?
1100
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Textbook Question
Given the Keq values for the following acid–base reactions, identify the strongest acid and the strongest base.
(a)
1113
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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
views