Textbook Question
Draw the conjugate acid of each of the following:
a. CH3CH2OH
b. CH3CH2O−
c.
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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 7a
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 7aChapter 3, Problem 7a
Butyric acid, the compound responsible for the unpleasant odor and taste of sour milk, has a pKa value of 4.82. What is its Ka value? Is it a stronger acid or a weaker acid than vitamin C?
Verified step by step guidance1
Identify the relationship between pKa and Ka. The formula to convert pKa to Ka is: \( K_a = 10^{-pK_a} \). This formula is derived from the logarithmic definition of pKa.
Substitute the given pKa value of butyric acid (4.82) into the formula: \( K_a = 10^{-4.82} \).
Calculate the value of \( 10^{-4.82} \) to determine the Ka value of butyric acid. This step involves using a calculator or logarithmic rules.
Compare the Ka value of butyric acid to the Ka value of vitamin C. Vitamin C has a pKa of approximately 4.10, so its Ka can be calculated using the same formula: \( K_a = 10^{-4.10} \).
Analyze the results: A lower pKa corresponds to a higher Ka, indicating a stronger acid. Compare the Ka values of butyric acid and vitamin C to determine which is the stronger acid.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
pKa and Ka Relationship
The pKa value is the negative logarithm of the acid dissociation constant (Ka) of a compound. It is calculated using the formula pKa = -log(Ka). A lower pKa value indicates a stronger acid, as it means the acid dissociates more completely in solution. To find Ka from pKa, you can use the equation Ka = 10^(-pKa).
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Identifying pKa values
Acid Strength Comparison
Acid strength is determined by the ability of an acid to donate protons (H+ ions) in solution. Stronger acids have higher Ka values and lower pKa values, indicating they dissociate more completely. To compare butyric acid with vitamin C, one must calculate the Ka values of both acids and analyze their dissociation tendencies in water.
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Butyric Acid and Vitamin C
Butyric acid (pKa 4.82) is a weak acid, while vitamin C (ascorbic acid) has a pKa around 4.1, indicating it is a stronger acid. By calculating the Ka values, one can determine that butyric acid has a lower dissociation constant than vitamin C, confirming that vitamin C is a stronger acid due to its greater tendency to donate protons in solution.
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Related Practice
Textbook Question
What is the conjugate base of each of the following?
1. NH3
2. HBr
3. HNO3
4. H2O
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Textbook Question
Antacids are compounds that neutralize stomach acid. Write the equations that show how Milk of Magnesia, Alka-Seltzer, and Tums remove excess acid.
a. Milk of Magnesia: Mg(OH)2
b. Alka-Seltzer: KHCO3 and NaHCO3
c. Tums: CaCO3
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Textbook Question
a. Which is a stronger acid: one with a pKa of 5.2 or one with a pKa of 5.8?
b. Which is a stronger acid: one with an acid dissociation constant of 3.4 × 10−3 or one with an acid dissociation constant of 2.1 × 10−4?
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Textbook Question
Estimate the pKa values of the following compounds:
c. CH3CH2COOH
d. CH3CH2CH2N+H3
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Textbook Question
An acid has a Ka of 4.53 × 10−6 in water. What is its Keq for reaction with water in a dilute solution? ([H2O] = 55.5 M)
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