Textbook Question
Which is a stronger acid?
c. <IMAGE>
d. CH3CH2CH2OH or CH3CH2CH2SH
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 30c,d
Bruice 8th EditionCh. 2 - Acids and Bases: Central to Understanding Organic ChemistryProblem 30c,dChapter 3, Problem 30c,d
Which is a stronger acid?
c. CH3OCH2CH2CH2OHorCH3CH2OCH2CH2OH
d. 
Verified step by step guidance1
Step 1: Analyze the molecular structures provided in the image. Both compounds (i) and (ii) are carboxylic acids, but they differ in the position of the hydroxyl group (-OH) relative to the carbonyl group (C=O). In (i), the hydroxyl group is on the second carbon, while in (ii), it is on the third carbon.
Step 2: Understand the concept of inductive effects. Electronegative groups like the hydroxyl group (-OH) can withdraw electron density through sigma bonds, stabilizing the conjugate base of the acid and increasing its acidity. The closer the electronegative group is to the acidic proton, the stronger the inductive effect.
Step 3: Compare the proximity of the hydroxyl group to the carboxylic acid functional group in both molecules. In compound (i), the hydroxyl group is closer to the carboxylic acid group, which means it will exert a stronger inductive effect compared to compound (ii).
Step 4: Predict the relative acidity based on the inductive effect. Since the hydroxyl group in compound (i) is closer to the acidic proton, it will stabilize the conjugate base more effectively, making compound (i) a stronger acid than compound (ii).
Step 5: Conclude that the position of the hydroxyl group significantly influences the acidity of the molecule due to the inductive effect. Compound (i) is the stronger acid compared to compound (ii).
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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 in organic chemistry is often measured by the pKa value, which indicates the strength of an acid. A lower pKa value corresponds to a stronger acid, meaning it can donate protons (H+) more readily. Understanding the relationship between structure and acidity is crucial, as factors like electronegativity and resonance can significantly influence pKa values.
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Identifying pKa values
Inductive Effect
The inductive effect refers to the electron-withdrawing or electron-donating influence of substituents on a molecule. Electronegative atoms or groups can stabilize the negative charge on the conjugate base of an acid, enhancing its acidity. In the comparison of acids, the presence of electron-withdrawing groups can lead to increased acidity due to this effect.
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01:47Understanding the Inductive Effect.
Resonance Stabilization
Resonance stabilization occurs when a molecule can be represented by multiple valid Lewis structures, allowing for the delocalization of electrons. This delocalization can stabilize the conjugate base formed after an acid donates a proton, making the original acid stronger. Analyzing the structures of the compounds in the question will reveal how resonance affects their acidity.
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03:43The radical stability trend.
Related Practice
Textbook Question
Which reaction in Problem 23 has the smallest equilibrium constant?
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Textbook Question
For each of the following compounds, indicate the atom that is protonated when an acid is added to a solution of the compound.
a.
b.
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Textbook Question
Which is a stronger base?
a.
b.
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Textbook Question
Rank the following from strongest base to weakest base:
b.
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Textbook Question
If HCl is a weaker acid than HBr, why is ClCH2COOH a stronger acid than BrCH2COOH?
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