Textbook Question
The following carboxylic acids were named incorrectly. Provide the correct name.
(b) 6-bromocyclohexane carboxylic acid
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Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids
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
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Mullins 1st EditionCh. 18 - Nucleophilic Acyl Substitution I: Carboxylic AcidsProblem 68
Mullins 1st EditionCh. 18 - Nucleophilic Acyl Substitution I: Carboxylic AcidsProblem 68Chapter 17, Problem 68
In Chapter 19, we will learn about the hydrolysis of t-butyl esters. In the reaction below, the hydrolysis is coupled to the decarboxylation reaction learned in this chapter. Suggest a mechanism for this reaction. [Hint: The formation of t-butanol proceeds by an SN1 reaction.]
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The reaction begins with the protonation of the ester carbonyl oxygen by the acid (H2SO4), increasing the electrophilicity of the carbonyl carbon.
Water, acting as a nucleophile, attacks the carbonyl carbon, leading to the formation of a tetrahedral intermediate.
The intermediate undergoes proton transfer to facilitate the departure of the t-butyl group, forming t-butanol. This step proceeds via an SN1 mechanism, where the t-butyl group leaves as a carbocation.
The carbocation is stabilized by the release of CO2, which occurs through decarboxylation. This step is facilitated by the acidic conditions and the formation of a stable cyclic ketone.
Finally, the cyclic ketone is formed as the product, along with the release of CO2 and t-butanol, completing the reaction mechanism.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrolysis of Esters
Hydrolysis of esters involves the reaction of an ester with water, leading to the formation of an alcohol and a carboxylic acid. This reaction can be catalyzed by acids or bases and is crucial in organic chemistry for understanding how esters can be converted back to their constituent components. The mechanism typically involves nucleophilic attack by water on the carbonyl carbon of the ester.
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SN1 Reaction Mechanism
The SN1 (Substitution Nucleophilic Unimolecular) mechanism is a two-step process where the rate-determining step involves the formation of a carbocation intermediate after the leaving group departs. This mechanism is characteristic of tertiary substrates, such as t-butyl esters, due to their ability to stabilize the carbocation. The subsequent step involves a nucleophile attacking the carbocation to form the final product.
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Decarboxylation
Decarboxylation is the process of removing a carboxyl group from a molecule, typically resulting in the release of carbon dioxide. This reaction is significant in organic synthesis and biochemistry, often occurring in the metabolism of fatty acids and amino acids. In the context of the question, decarboxylation may be coupled with hydrolysis to facilitate the formation of t-butanol and other products.
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Related Practice
Textbook Question
When a chemist attempted the following reaction sequence, the desired product was not formed.
(a) Why?
(b) Suggest a solution to the problem. [Think about chemistry from the end of Chapter 13.]
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Textbook Question
While acidic conditions were used in Assessment 18.68, decarboxylation of esters can also be conducted under basic conditions to give, at least temporarily, the enolate product shown. [We’ll learn more about the chemistry of enolates in Chapter 20.] Suggest a mechanism of this reaction. [Hint: The formation of chloromethane proceeds by an SN2 reaction.]
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Textbook Question
The absence of what band in the IR spectrum of the product in Figure 18.59 would be consistent with full conversion of the carboxylic acid to an acid chloride?
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