Textbook Question
b. How does the presence of an electronegative substituent such as Cl affect the acidity of a carboxylic acid?
c. How does the location of the substituent affect the acidity of the carboxylic acid?
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 59
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 59Chapter 3, Problem 59
Rank the following compounds from strongest to weakest acid:
CH3CH2OH; CH3CH2NH2; CH3CH2SH; CH3CH2CH3
Verified step by step guidance1
Step 1: Understand the concept of acidity. Acidity is determined by the ability of a compound to donate a proton (H⁺). The more stable the conjugate base after losing a proton, the stronger the acid.
Step 2: Analyze the functional groups in each compound. CH3CH2OH contains an alcohol (-OH) group, CH3CH2NH2 contains an amine (-NH2) group, CH3CH2SH contains a thiol (-SH) group, and CH3CH2CH3 is an alkane with no acidic functional group.
Step 3: Compare the electronegativity of the atoms directly bonded to hydrogen in each functional group. Oxygen in CH3CH2OH is more electronegative than sulfur in CH3CH2SH, and sulfur is more electronegative than nitrogen in CH3CH2NH2. Electronegativity affects the stability of the conjugate base.
Step 4: Consider the polarizability of the atoms. Sulfur in CH3CH2SH is larger and more polarizable than oxygen in CH3CH2OH, which can stabilize the conjugate base better, making thiols generally more acidic than alcohols.
Step 5: Evaluate CH3CH2CH3. Alkanes like CH3CH2CH3 lack acidic functional groups and are extremely weak acids. Rank the compounds based on the above analysis: CH3CH2SH > CH3CH2OH > CH3CH2NH2 > CH3CH2CH3.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acidity and pKa
Acidity refers to the ability of a compound to donate a proton (H+). The strength of an acid is often measured by its pKa value; lower pKa values indicate stronger acids. Understanding the relationship between structure and acidity is crucial, as factors like electronegativity and resonance can influence a compound's ability to stabilize the negative charge of its conjugate base.
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Identifying pKa values
Functional Groups and Their Effects
Different functional groups have varying effects on acidity. For example, alcohols (like CH3CH2OH) can donate protons due to the hydroxyl (-OH) group, while amines (like CH3CH2NH2) are generally basic and less acidic. Thiols (like CH3CH2SH) are more acidic than alcohols due to the lower electronegativity of sulfur compared to oxygen, which stabilizes the conjugate base.
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02:36Identifying Functional Groups
Inductive Effect and Hybridization
The inductive effect refers to the electron-withdrawing or electron-donating effects of substituents on acidity. Electronegative atoms can stabilize the negative charge of a conjugate base, enhancing acidity. Additionally, the hybridization of the atom bearing the acidic proton affects acidity; sp-hybridized carbons are more acidic than sp2 or sp3 due to increased s-character, which holds the electrons closer to the nucleus.
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Related Practice
Textbook Question
Explain the relative acidities.
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Textbook Question
Draw the products of the following reactions:
a.
b.
c.
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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
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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