Textbook Question
Peroxyacetic acid (pKa = 8.2) is a much weaker acid than acetic acid (pKa = 4.74). Explain why peroxyacetic acid is a weaker acid than acetic acid.
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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 42a,b
Predict the products of the following acid–base reactions.
(a) H2SO4 + CH3COO– ⇌
(b) CH3COOH + (CH3)3N: ⇌
Verified step by step guidance1
Identify the acid and base in each reaction. In reaction (a), H2SO4 is the acid and CH3COO- is the base. In reaction (b), CH3COOH is the acid and (CH3)3N is the base.
Determine the conjugate base of the acid and the conjugate acid of the base. For reaction (a), the conjugate base of H2SO4 is HSO4-. For reaction (b), the conjugate acid of (CH3)3N is (CH3)3NH+.
Write the products of the acid-base reaction. In reaction (a), the products are HSO4- and CH3COOH. In reaction (b), the products are CH3COO- and (CH3)3NH+.
Consider the equilibrium position. The strength of the acids and bases involved will determine the direction of the equilibrium. H2SO4 is a strong acid, so the equilibrium in reaction (a) will favor the formation of products. CH3COOH is a weak acid, so the equilibrium in reaction (b) may favor the reactants.
Review the reaction mechanism. In reaction (a), the proton transfer from H2SO4 to CH3COO- forms HSO4- and CH3COOH. In reaction (b), the proton transfer from CH3COOH to (CH3)3N forms CH3COO- and (CH3)3NH+.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Reaction
Acid-base reactions involve the transfer of protons (H+) from an acid to a base. In organic chemistry, these reactions often result in the formation of a conjugate acid and a conjugate base. Understanding the strength and structure of the acids and bases involved is crucial for predicting the products.
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02:49
The Lewis definition of acids and bases.
Conjugate Acid-Base Pairs
A conjugate acid-base pair consists of two species that differ by a proton. When an acid donates a proton, it forms its conjugate base, and when a base accepts a proton, it forms its conjugate acid. Identifying these pairs helps in predicting the direction and products of acid-base reactions.
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2:56Base Pairing Concept 1
pKa Values
The pKa value is a measure of the acidity of a compound, indicating how easily it donates a proton. Lower pKa values correspond to stronger acids. Comparing the pKa values of the acids involved in a reaction helps determine the equilibrium position and the predominant species in the reaction mixture.
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07:45Identifying pKa values
Related Practice
Textbook Question
The following compound can become protonated on any of the three nitrogen atoms. One of these nitrogens is much more basic than the others, however.
b. Determine which nitrogen atom is the most basic.
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Textbook Question
The following compounds are listed in increasing order of acidity. In each case, the most acidic proton is shown in red.
b. Explain why X is a stronger acid than W.
c. Explain why Y is a stronger acid than X.
d. Explain why Z is a stronger acid than Y.
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Textbook Question
Hydrogen peroxide (HOOH) has a pKa of 11.6, making it roughly 10,000 times as strong an acid as water (pKa = 15.7). Explain why H2O2 is a stronger acid than H2O.
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Textbook Question
Predict the products of the following acid–base reactions.
(e) H2O + NH3 ⇌
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Textbook Question
Predict the products of the following acid–base reactions.
(c)
(d)
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