Textbook Question
Rank the following alcohols from strongest to weakest acid.
CH2═CHCH2OH; CH3CH2CH2OH; HC≡CCH2OH
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Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 61a
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 61aChapter 3, Problem 61a
Give the products of the following acid–base reactions and indicate whether reactants or products are favored at equilibrium.
a. 
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Identify the acid and base on both sides of the reaction. The acid is the species that donates a proton (H⁺), and the base is the species that accepts a proton.
Determine the conjugate acid and conjugate base formed after the proton transfer. The acid loses a proton to form its conjugate base, and the base gains a proton to form its conjugate acid.
Use the pKa values provided in Section 2.3 to compare the acidity of the acid on the reactant side and the conjugate acid on the product side. Recall that a lower pKa value indicates a stronger acid.
Determine the direction of equilibrium by comparing the strengths of the acids. Equilibrium favors the side with the weaker acid (higher pKa value).
Write the products of the reaction, clearly indicating the conjugate acid and conjugate base, and state whether the equilibrium favors the reactants or products based on the pKa comparison.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Reactions
Acid-base reactions involve the transfer of protons (H+) between reactants. An acid donates a proton, while a base accepts it. Understanding the nature of the acids and bases involved is crucial for predicting the products of the reaction and determining the direction of equilibrium.
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02:49
The Lewis definition of acids and bases.
pKa and Equilibrium
The pKa value is a measure of the strength of an acid; lower pKa values indicate stronger acids. In acid-base reactions, the equilibrium position can be predicted by comparing the pKa values of the acids and their conjugate bases. The reaction favors the side with the weaker acid (higher pKa) at equilibrium.
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02:19The relationship between equilibrium constant and pKa.
Equilibrium Position
The equilibrium position of a reaction indicates the relative concentrations of reactants and products at equilibrium. In acid-base reactions, the favored side is determined by the stability of the resulting species, which is influenced by factors such as electronegativity and resonance. Understanding these concepts helps in predicting the outcome of the reaction.
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2:49Reactions at the Allylic Position Concept 5
Related Practice
Textbook Question
Explain the relative acidities.
CH2═CHCH2OH, CH3CH2CH2OH, HC≡CCH2OH
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Textbook Question
Give the products of the following acid–base reactions and indicate whether reactants or products are favored at equilibrium.
b. CH3CH2OH + -NH2 ⇌
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Textbook Question
For each of the following compounds, draw the form that predominates at pH = 3, pH = 6, pH = 10, and pH = 14:
c. CF3CH2OH (pKa = 12.4)
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Textbook Question
For each of the following compounds, draw the form that predominates at pH = 3, pH = 6, pH = 10, and pH = 14:
a. CH3COOH (pKa = 4.8)
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Textbook Question
For each of the following compounds, draw the form that predominates at pH = 3, pH = 6, pH = 10, and pH = 14:
b. CH3CH2N+H3 (pKa = 11.0)
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