Textbook Question
Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.
(g) KOH + CH3CH2OH ⇌
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Ch.10 - Structure and Synthesis of Alcohols
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 10, Problem 42e
Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.
(e) (CH3)3C–O– + CH3CH2OH ⇌
Verified step by step guidance1
Step 1: Identify the acid and base on both sides of the reaction. In this case, (CH3)3C—O⁻ is the base, and CH3CH2OH is the acid. The conjugate acid and base will form on the product side.
Step 2: Determine the conjugate acid and conjugate base. The conjugate acid of (CH3)3C—O⁻ is (CH3)3C—OH, and the conjugate base of CH3CH2OH is CH3CH2O⁻.
Step 3: Compare the acidity of the acids involved. (CH3)3C—OH is a weaker acid compared to CH3CH2OH because the bulky tert-butyl group stabilizes the conjugate base (CH3)3C—O⁻ through steric hindrance and inductive effects.
Step 4: Use the pKa values to predict the direction of equilibrium. CH3CH2OH has a lower pKa (stronger acid) compared to (CH3)3C—OH, so the equilibrium will favor the formation of the weaker acid and weaker base, which are (CH3)3C—OH and CH3CH2O⁻.
Step 5: Conclude that the equilibrium favors the products because the reaction moves toward the side with the weaker acid and weaker base, which are more stable.
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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 organic chemistry, acids are proton donors, while bases are proton acceptors. Understanding the nature of the acids and bases involved is crucial for predicting the direction of the equilibrium and the products formed in the reaction.
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The Lewis definition of acids and bases.
Equilibrium Position
The position of equilibrium in a chemical reaction indicates whether the reactants or products are favored. This can be influenced by factors such as the strength of the acids and bases involved, the stability of the resulting products, and the reaction conditions. Analyzing these factors helps determine the predominant species at equilibrium.
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Stability of Conjugate Acids and Bases
The stability of the conjugate acids and bases formed during an acid-base reaction plays a significant role in determining the equilibrium position. A more stable conjugate base corresponds to a stronger acid, and vice versa. Evaluating the stability of these species can provide insight into which side of the reaction is favored.
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Related Practice
Textbook Question
Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.
(f) (CH3)3C–O– + H2O ⇌
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Textbook Question
Show how you would synthesize the following:
f. 2,5-dimethylhexane from a four-carbon alkyl halide
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Textbook Question
Complete the following acid–base reactions. In each case, indicate whether the equilibrium favors the reactants or the products, and explain your reasoning.
(d)
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Textbook Question
Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.
(a) octan-1-ol
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Textbook Question
Show how you would synthesize the following:
e. cis-pent-2-en-1-thiol from a suitable alkenyl halide
727
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