Textbook Question
What products are formed when each of the following reacts with HO−?
e. +CH3
f. FeBr3
3
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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 52a,b
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 52a,bChapter 3, Problem 52a,b
What products are formed when each of the following reacts with HO−?
a. CH3OH
b. +NH4
Verified step by step guidance1
Step 1: Analyze the reaction of CH3OH (methanol) with HO− (hydroxide ion). Methanol is a weak acid, and hydroxide ion is a strong base. The hydroxide ion can deprotonate the hydroxyl group (-OH) of methanol, forming methoxide ion (CH3O−) and water (H2O). Write the reaction as: CH3OH + HO− → CH3O− + H2O.
Step 2: Consider the reaction of +NH4 (ammonium ion) with HO−. The ammonium ion is a weak acid, and hydroxide ion is a strong base. The hydroxide ion can deprotonate the ammonium ion, forming ammonia (NH3) and water (H2O). Write the reaction as: +NH4 + HO− → NH3 + H2O.
Step 3: For both reactions, identify the acid-base pairs. In the first reaction, CH3OH is the acid, and CH3O− is its conjugate base. In the second reaction, +NH4 is the acid, and NH3 is its conjugate base.
Step 4: Confirm that the reactions proceed in the direction that favors the formation of the weaker acid and base. In both cases, the products (CH3O− and NH3) are weaker bases compared to the reactants (HO−), and the reactions are thermodynamically favorable.
Step 5: Summarize the products formed. For part (a), the products are CH3O− and H2O. For part (b), the products are NH3 and H2O. Ensure the reactions are balanced and consistent with acid-base chemistry principles.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile, such as hydroxide ion (HO−), attacks a carbon atom, replacing a leaving group. In the case of CH3OH (methanol), the hydroxide ion can replace the hydroxyl group, leading to the formation of methoxide ion (CH3O−). Understanding this mechanism is crucial for predicting the products of reactions involving nucleophiles.
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01:47
Nucleophiles and Electrophiles can react in Substitution Reactions.
Ammonium Ion Reactivity
The ammonium ion (NH4+) is a positively charged species that can participate in acid-base reactions. When it reacts with HO−, it can undergo deprotonation, resulting in the formation of ammonia (NH3) and water. Recognizing the behavior of ammonium ions in the presence of strong bases is essential for predicting the outcome of such reactions.
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2:18Metal Ion Catalysis Example 1
Acid-Base Reactions
Acid-base reactions involve the transfer of protons (H+) between species. In this context, HO− acts as a strong base, capable of accepting protons from acids like NH4+. Understanding the principles of acid-base chemistry helps in predicting the products formed when different organic compounds interact with hydroxide ions.
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02:49The Lewis definition of acids and bases.
Related Practice
Textbook Question
Explain the relative acidities.
3
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Textbook Question
Given the data in Problem 47:
b. What pH would you make the water layer to cause the carboxylic acid to dissolve in the water layer and the amine to dissolve in the ether layer?
1
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Textbook Question
Draw the products of the following reactions. Use curved arrows to show where the pair of electrons starts and where it ends up.
a.
b.
5
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Textbook Question
Write the equation that shows how a buffer made by dissolving CH3COOH and CH3COO−Na+ in water prevents the pH of a solution from changing appreciably when
a. a small amount of H+ is added to the solution.
b. a small amount of HO− is added to the solution.
1
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Textbook Question
What products are formed when each of the following reacts with HO−?
c. CH3N+H3
d. BF3