Textbook Question
What is the conjugate base of each of the following acids? [The most acidic proton is indicated.]
(c)
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 9d
What is the conjugate base of each of the following acids? [The most acidic proton is indicated.]
(d) 
Verified step by step guidance1
Identify the acidic proton in the molecule. In this case, the blue arrow points to the hydrogen atom attached to the oxygen in the hydroxyl (-OH) group.
Recall that the conjugate base is formed by removing the most acidic proton from the molecule. This involves deprotonation of the hydroxyl group.
Write the chemical equation for the deprotonation process: \( \text{R-OH} \rightarrow \text{R-O}^- + \text{H}^+ \), where \( \text{R} \) represents the cyclohexyl group.
Recognize that the conjugate base of the acid is the cyclohexoxide ion (\( \text{R-O}^- \)), which is the cyclohexyl group bonded to an oxygen atom carrying a negative charge.
Ensure that the negative charge on the oxygen is properly represented, as it results from the loss of the proton during deprotonation.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Chemistry
Acid-base chemistry involves the transfer of protons (H+) between species. An acid is defined as a proton donor, while a base is a proton acceptor. Understanding this concept is crucial for identifying conjugate acid-base pairs, where the conjugate base is formed when an acid donates a proton.
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02:49
The Lewis definition of acids and bases.
Conjugate Base
The conjugate base of an acid is what remains after the acid has donated a proton. For example, when phenol (C6H5OH) donates its acidic proton from the hydroxyl group, it forms the phenoxide ion (C6H5O-), which is its conjugate base. Recognizing the structure of the conjugate base is essential for predicting its reactivity and properties.
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03:27Conjugated states
Resonance Stabilization
Resonance stabilization refers to the delocalization of electrons across multiple atoms in a molecule, which can enhance stability. In the case of phenoxide ion, the negative charge on the oxygen can be delocalized into the aromatic ring, making the conjugate base more stable than if the charge were localized. This concept is important for understanding the acidity of phenols compared to other alcohols.
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03:43The radical stability trend.
Related Practice
Textbook Question
Identify the acid from which the following conjugate bases were formed. [The most basic atom is indicated.]
(c)
Textbook Question
What is the conjugate base of each of the following acids? [The most acidic proton is indicated.]
(a)
2
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Textbook Question
Sulfuric acid is a very strong acid. Show how the following equation can be used to explain that sulfuric acid is at once an Arrhenius, Brønsted–Lowry, and Lewis acid.
Textbook Question
What is the conjugate acid of each of the following bases? [The most basic atom is indicated.]
(d)
Textbook Question
What is the conjugate acid of each of the following bases? [The most basic atom is indicated.]
(a)
1
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