Textbook Question
Draw the products of the following reactions:
a.
b.
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 60b
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 60bChapter 3, Problem 60b
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)
Verified step by step guidance1
Step 1: Understand the relationship between pH and pKa. The pKa value indicates the pH at which half of the species is protonated and half is deprotonated. When pH < pKa, the species is predominantly protonated. When pH > pKa, the species is predominantly deprotonated.
Step 2: Analyze the given compound CH3CH2N+H3. This is an ethylammonium ion, which can lose a proton to form CH3CH2NH2. The pKa of the protonated form (CH3CH2N+H3) is given as 11.0.
Step 3: Determine the predominant form at pH=3. Since pH=3 is much lower than the pKa (11.0), the compound will remain fully protonated as CH3CH2N+H3.
Step 4: Determine the predominant form at pH=6. Since pH=6 is still lower than the pKa (11.0), the compound will predominantly remain protonated as CH3CH2N+H3.
Step 5: Determine the predominant forms at pH=10 and pH=14. At pH=10, which is slightly below the pKa, the compound will still be mostly protonated as CH3CH2N+H3, but some deprotonation to CH3CH2NH2 will occur. At pH=14, which is much higher than the pKa, the compound will be fully deprotonated as CH3CH2NH2.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Chemistry
Acid-base chemistry involves the transfer of protons (H+) between species. The pH of a solution indicates its acidity or basicity, with lower pH values representing acidic conditions and higher values indicating basic conditions. Understanding how acids and bases behave in different pH environments is crucial for predicting the predominant form of a compound.
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The Lewis definition of acids and bases.
pKa and its Significance
The pKa value is a measure of the strength of an acid in solution, representing the pH at which half of the species are deprotonated. A lower pKa indicates a stronger acid. In this case, with a pKa of 11.0, the compound CH3CH2N+H3 will predominantly exist in its protonated form at lower pH values (like pH 3 and 6) and will start to deprotonate as the pH increases beyond its pKa.
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Protonation and Deprotonation
Protonation refers to the addition of a proton (H+) to a molecule, while deprotonation is the removal of a proton. The state of a compound can change based on the pH of the solution; at low pH, compounds are more likely to be protonated, while at high pH, they tend to lose protons. For CH3CH2N+H3, this means it will remain protonated at acidic pH levels and begin to lose protons as the pH rises past its pKa.
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Related Practice
Textbook Question
Rank the following compounds from strongest to weakest acid:
CH3CH2OH; CH3CH2NH2; CH3CH2SH; CH3CH2CH3
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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.
b. CH3CH2OH + -NH2 ⇌
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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:
a. CH3COOH (pKa = 4.8)
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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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