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 61b
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 61bChapter 3, Problem 61b
Give the products of the following acid–base reactions and indicate whether reactants or products are favored at equilibrium.
b. CH3CH2OH + -NH2 ⇌
Verified step by step guidance1
Step 1: Identify the acid and base in the reaction. CH3CH2OH (ethanol) acts as the acid because it can donate a proton (H+), and NH2⁻ (amide ion) acts as the base because it can accept a proton.
Step 2: Write the conjugate acid and conjugate base formed after the proton transfer. When CH3CH2OH donates a proton, it forms CH3CH2O⁻ (ethoxide ion). When NH2⁻ accepts a proton, it forms NH3 (ammonia). The reaction can be written as: CH3CH2OH + NH2⁻ ⇌ CH3CH2O⁻ + NH3.
Step 3: Use the pKa values to determine the strength of the acids and bases. The pKa of CH3CH2OH is approximately 16, and the pKa of NH3 is approximately 38. Lower pKa values indicate stronger acids.
Step 4: Compare the pKa values of the acids on both sides of the equilibrium. Since CH3CH2OH (pKa = 16) is a stronger acid than NH3 (pKa = 38), the equilibrium will favor the formation of the weaker acid and base, which are NH3 and CH3CH2O⁻.
Step 5: Conclude that the products (CH3CH2O⁻ and NH3) are favored at equilibrium because the reaction shifts toward the side with the weaker acid and base.
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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. In these reactions, acids donate protons while bases accept them. Understanding the nature of the reactants, including their acidity and basicity, is crucial for predicting the products and the direction of the 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 bases involved. The reaction will favor the formation of the weaker acid and base, which corresponds to the higher pKa value.
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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, if the products are favored, it means that the reaction proceeds to the right, forming more products. Conversely, if the reactants are favored, the equilibrium lies to the left, indicating that the original substances are more stable.
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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
A single bond between two carbons with different hybridizations has a small dipole. What is the direction of the dipole in the indicated bonds?
a.
b.
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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:
b. CH3CH2N+H3 (pKa = 11.0)
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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.
a.
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