Textbook Question
The following compounds can all react as bases.
a. For each compound, show its conjugate acid. Show any resonance forms if applicable.
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Ch. 2 - Acids and Bases; Functional Groups
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- 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
Chapter 2, Problem 46b
The following compounds can all react as bases.
b. Rank the conjugate acids in the order you would predict, from most stable to least stable.
Verified step by step guidance1
Identify the conjugate acids of each base. For each base, add a proton (H⁺) to the atom that can accept it. For example, for CH₃CH₂NH₂, the conjugate acid is CH₃CH₂NH₃⁺.
Consider the stability of each conjugate acid. Stability is often influenced by factors such as resonance, inductive effects, and the electronegativity of the atom bearing the positive charge.
Evaluate the resonance stabilization. For example, the conjugate acid of CH₃CONH₂ can be resonance stabilized due to the adjacent carbonyl group.
Assess the inductive effects. Electronegative atoms or groups can stabilize a positive charge through the inductive effect. For instance, the presence of an electronegative oxygen in CH₃CH₂OH can stabilize the conjugate acid.
Rank the conjugate acids from most stable to least stable based on the above evaluations. Consider the overall effect of resonance, inductive effects, and electronegativity on the stability of each conjugate acid.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Conjugate Acid-Base Pairs
In acid-base chemistry, a conjugate acid-base pair consists of two species that transform into each other by the gain or loss of a proton (H+). When a base gains a proton, it forms its conjugate acid. Understanding the stability of conjugate acids is crucial for predicting the strength of the original bases, as more stable conjugate acids correspond to weaker bases.
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Base Pairing Concept 1
Acid Stability and Resonance
The stability of a conjugate acid is often influenced by resonance, which delocalizes charge over multiple atoms, reducing the energy of the molecule. For example, amides can stabilize their conjugate acids through resonance between the nitrogen and the carbonyl group, making them more stable compared to non-resonance-stabilized species. This concept helps in ranking the stability of conjugate acids.
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Electronegativity and Inductive Effects
Electronegativity and inductive effects play a significant role in acid stability. Electronegative atoms or groups can stabilize a conjugate acid by withdrawing electron density through sigma bonds, known as the inductive effect. This effect can enhance the stability of a conjugate acid by dispersing charge, making it a key factor in determining the relative stability of different conjugate acids.
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Related Practice
Textbook Question
The following compounds can all react as bases.
c. Rank the original compounds in order, from strongest base to weakest base.
1759
views
Textbook Question
The following compounds can all react as acids.
a. For each compound, show its conjugate base. Show any resonance forms if applicable.
1004
views
Textbook Question
The following compounds can all react as acids.
a. For each compound, show its conjugate base. Show any resonance forms if applicable. b. Rank the conjugate bases in the order you would predict, from most stable to least stable.
1427
views
Textbook Question
The following compounds can all react as acids.
b. Rank the conjugate bases in the order you would predict, from most stable to least stable.
878
views
Textbook Question
The following compounds can all react as acids.
c. Rank the original compounds in order, from strongest acid to weakest acid.
1742
views