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 66c
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(c) 
Verified step by step guidance1
Identify the functional groups in the molecule. The structure contains a hydroxyl group (-OH) on the left side and a carboxylic acid group (-COOH) on the right side.
Determine the reactivity of the functional groups with a strong base. A strong base will deprotonate the most acidic hydrogen in the molecule. The carboxylic acid group is more acidic than the hydroxyl group due to resonance stabilization of the carboxylate anion.
Predict the site of deprotonation. The hydrogen attached to the oxygen in the carboxylic acid group will be removed by the strong base, forming a carboxylate anion (R-COO⁻).
Write the resulting structure after deprotonation. Replace the hydrogen in the carboxylic acid group with a negative charge on the oxygen atom, indicating the formation of the carboxylate anion.
Consider the stability of the product. The carboxylate anion is stabilized by resonance, making it the favored product of the reaction with a strong base.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Strong Bases in Organic Chemistry
Strong bases, such as sodium hydroxide (NaOH) or potassium tert-butoxide (KOtBu), are capable of deprotonating weak acids. In organic chemistry, they are often used to initiate reactions by removing protons from functional groups, such as alcohols or carboxylic acids, leading to the formation of alkoxides or carboxylate ions.
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Deprotonation of Alcohols
Alcohols contain hydroxyl (-OH) groups that can act as weak acids. When a strong base is introduced, it can deprotonate the alcohol, resulting in the formation of an alkoxide ion. This process is crucial in many organic reactions, as the alkoxide can act as a nucleophile in subsequent steps.
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Reaction Mechanisms
Understanding reaction mechanisms is essential for predicting the products of chemical reactions. In this case, the mechanism involves the deprotonation of hydroxyl groups by a strong base, leading to the formation of reactive intermediates that can further react with other molecules, ultimately determining the final product of the reaction.
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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.
(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.
(f)
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
For each of the following molecules, predict the product that would form upon reaction of a single equivalent of a strong base.
(b)
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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