Textbook Question
Does methanol behave as an acid or a base when it reacts with methylamine?
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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 10a,b,c
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 10a,b,cChapter 3, Problem 10a,b,c
Draw the conjugate acid of each of the following:
a. CH3CH2OH
b. CH3CH2O−
c. 
Verified step by step guidance1
Identify the concept of a conjugate acid: A conjugate acid is formed when a base accepts a proton (H⁺). For each compound, determine the site where a proton can be added.
For CH₃CH₂OH (ethanol): The molecule contains an -OH group, which can act as a base. Add a proton (H⁺) to the oxygen atom, resulting in CH₃CH₂OH₂⁺. This is the conjugate acid of ethanol.
For CH₃CH₂O⁻ (ethoxide ion): The molecule is already negatively charged, indicating it is a strong base. Add a proton (H⁺) to the oxygen atom, neutralizing the negative charge and forming CH₃CH₂OH. This is the conjugate acid of the ethoxide ion.
Draw the structures of the conjugate acids: For CH₃CH₂OH₂⁺, the oxygen will have a positive charge due to the addition of the proton. For CH₃CH₂OH, the structure remains the same as ethanol since it is the neutral conjugate acid of ethoxide.
Verify the results: Ensure that the conjugate acids are correctly formed by checking that a single proton (H⁺) has been added to the base in each case, and the charges are consistent with the addition of the proton.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Conjugate Acids and Bases
In acid-base chemistry, a conjugate acid is formed when a base gains a proton (H+). Conversely, a conjugate base is what remains after an acid donates a proton. Understanding this relationship is crucial for predicting the behavior of substances in chemical reactions, particularly in organic chemistry where proton transfer is common.
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Equilibrium constant and conjugates.
Alcohols and Their Protonation
Alcohols, like CH3CH2OH (ethanol), can act as weak acids. When they are protonated, they form their conjugate acids, which are typically oxonium ions. This concept is important for understanding the reactivity of alcohols in various chemical reactions, including their role in nucleophilic substitutions and eliminations.
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Alkoxide Ions
Alkoxide ions, such as CH3CH2O− (ethoxide), are the conjugate bases of alcohols. They are formed when an alcohol donates a proton. Recognizing the properties and reactivity of alkoxide ions is essential for understanding their role in organic synthesis, particularly in reactions involving nucleophiles and bases.
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Related Practice
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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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 base: CH3COO− or HCOO−? (The pKa of CH3COOH is 4.8; the pKa of HCOOH is 3.8.)
b. Which is a stronger base: HO− or -NH2? (The pKa of H2O is 15.7; the pKa of NH3 is 36.)
c. Which is a stronger base: H2O or CH3OH? (The pKa of H3O+ is −1.7; the pKa of CH3O+H2 is −2.5.)
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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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