Textbook Question
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(d)
1
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Ch. 4 - Acids and Bases: Electron Flow
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 3, Problem 66b
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(b) 
Verified step by step guidance1
Identify the functional groups in the molecule. The structure contains two carboxylic acid groups (-COOH) and a chlorine atom attached to the cyclohexane ring.
Determine the reactivity of the molecule with a strong base. Carboxylic acids are acidic and will react with a strong base to form their conjugate base, the carboxylate anion (-COO⁻). The chlorine atom may also influence the reactivity due to its electron-withdrawing nature.
Predict the reaction of the strong base with the carboxylic acid groups. A single equivalent of a strong base will deprotonate one of the carboxylic acid groups, forming a carboxylate anion and leaving the other carboxylic acid group intact.
Consider the position of the chlorine atom. The chlorine atom is electron-withdrawing and may stabilize the carboxylate anion formed near it, making the carboxylic acid group closer to the chlorine more likely to be deprotonated.
Write the expected product. The molecule will have one carboxylic acid group converted to a carboxylate anion (-COO⁻), while the other carboxylic acid group remains unchanged. The chlorine atom remains attached to the cyclohexane ring.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Reactions
Acid-base reactions involve the transfer of protons (H+) between reactants. In organic chemistry, strong bases can deprotonate acidic functional groups, such as alcohols or carboxylic acids, leading to the formation of alkoxide ions or carboxylate ions. Understanding the acidity of functional groups is crucial for predicting the products of these reactions.
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The Lewis definition of acids and bases.
Nucleophilic Substitution
Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the provided molecule, the chlorine atom is a good leaving group, and when a strong base is present, it can facilitate the substitution reaction, leading to the formation of new products.
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01:47Nucleophiles and Electrophiles can react in Substitution Reactions.
Functional Group Reactivity
Different functional groups exhibit varying reactivities based on their electronic properties. In the given molecule, the presence of hydroxyl (-OH) and carbonyl (C=O) groups influences how the molecule interacts with a strong base. Recognizing the reactivity of these groups is essential for predicting the outcome of the reaction and the stability of the resulting products.
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02:36Identifying Functional Groups
Related Practice
Textbook Question
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(c)
Textbook Question
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(a)
1
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Textbook Question
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(e)
2
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Textbook Question
Identify the stronger acid in each pair. Explain your choice. Citing pKa values is not an acceptable answer.
(a)
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Textbook Question
Benzoic acid and phenol are insoluble in water. When sodium bicarbonate is added to the water, benzoic acid dissolves, but phenol does not. The addition of sodium hydroxide causes both to dissolve. On the basis of these observations, estimate the pKa of phenol. [The pKa of H2CO3 is 6.4.]
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