Textbook Question
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?
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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 4b
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 4bChapter 3, Problem 4b
What is the conjugate base of each of the following?
1. NH3
2. HBr
3. HNO3
4. H2O
Verified step by step guidance1
Step 1: Understand the concept of a conjugate base. A conjugate base is formed when an acid donates a proton (H⁺). The conjugate base will have one less hydrogen atom and a negative charge compared to the original acid.
Step 2: For NH₃ (ammonia), identify the acid and remove one proton (H⁺). The conjugate base will be NH₂⁻. This is because NH₃ loses a hydrogen atom and gains a negative charge.
Step 3: For HBr (hydrobromic acid), remove one proton (H⁺) from the molecule. The conjugate base will be Br⁻, as HBr loses its hydrogen atom and becomes negatively charged.
Step 4: For HNO₃ (nitric acid), remove one proton (H⁺) from the molecule. The conjugate base will be NO₃⁻, as HNO₃ loses its hydrogen atom and gains a negative charge.
Step 5: For H₂O (water), remove one proton (H⁺) from the molecule. The conjugate base will be OH⁻, as H₂O loses a hydrogen atom and becomes negatively charged.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Conjugate Acid-Base Theory
The conjugate acid-base theory, developed by Brønsted and Lowry, defines acids as proton donors and bases as proton acceptors. When an acid donates a proton (H+), it forms its conjugate base, while the base that accepts the proton becomes its conjugate acid. Understanding this relationship is crucial for identifying conjugate pairs in chemical reactions.
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Equilibrium constant and conjugates.
Ammonia (NH3) and its Conjugate Base
Ammonia (NH3) acts as a weak base in aqueous solutions. When it accepts a proton, it forms its conjugate acid, ammonium (NH4+). The conjugate base of ammonia, however, is the amide ion (NH2-), which is formed when ammonia donates a proton. Recognizing this transformation is essential for solving the question.
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Strong Acids and Their Conjugate Bases
Strong acids, such as HBr and HNO3, completely dissociate in water, meaning they donate protons readily. The conjugate bases of strong acids are typically very weak and have negligible basicity. For example, the conjugate base of HBr is bromide ion (Br-), and for HNO3, it is nitrate ion (NO3-). Understanding the strength of acids and their corresponding conjugate bases is vital for this question.
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Related Practice
Textbook Question
What is the conjugate acid of each of the following?
1. NH3
2. Cl−
3. HO−
4. H2O
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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
Consider the following reaction:
HBr + -C≡N ⇌ Br− + HC≡N
c. What is the conjugate base of the acid on the left?
d. What is the conjugate acid of the base on the left?
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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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Textbook Question
Consider the following reaction:
HBr + -C≡N ⇌ Br− + HC≡N
g. What is the conjugate base of the acid on the right?
h. What is the conjugate acid of the base on the right?
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