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 59
Mullins 1st EditionCh. 18 - Nucleophilic Acyl Substitution I: Carboxylic AcidsProblem 59Chapter 17, Problem 59
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.]
Verified step by step guidance1
The reaction sequence involves the formation of a Grignard reagent from the bromide compound. The first step is the reaction of the alkyl bromide with magnesium in diethyl ether (Et₂O) to form the Grignard reagent. This reagent is highly reactive and can be used to form carbon-carbon bonds.
The presence of the hydroxyl group (OH) in the starting material is problematic because Grignard reagents are strong bases and will react with the acidic hydrogen of the hydroxyl group, leading to the formation of an alkoxide rather than the desired Grignard reagent.
To solve this problem, the hydroxyl group should be protected before the formation of the Grignard reagent. A common method is to convert the alcohol into a silyl ether using a reagent like trimethylsilyl chloride (TMSCl) in the presence of a base such as imidazole.
Once the hydroxyl group is protected, the Grignard reagent can be formed without interference from the acidic hydrogen. The Grignard reagent can then react with carbon dioxide (CO₂) to form the carboxylate intermediate.
Finally, the carboxylate intermediate is quenched with an acid, such as H₃O⁺, to yield the carboxylic acid product. After the reaction is complete, the protecting group can be removed to regenerate the hydroxyl group, yielding the desired product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reaction Mechanisms
Understanding reaction mechanisms is crucial in organic chemistry as it describes the step-by-step process by which reactants transform into products. Each mechanism outlines the movement of electrons, the formation and breaking of bonds, and the intermediates involved. A clear grasp of these mechanisms helps chemists predict the outcomes of reactions and troubleshoot when desired products are not formed.
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Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing the functional groups present in reactants and products is essential for predicting reactivity and understanding how changes in these groups can affect the outcome of a reaction. This knowledge is vital when suggesting modifications to achieve the desired product.
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Stereochemistry
Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. The three-dimensional orientation of functional groups can significantly influence reaction pathways and product formation. Understanding stereochemistry is important for addressing issues related to selectivity and yield in organic reactions, particularly when the desired product has specific stereochemical requirements.
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Related Practice
Textbook Question
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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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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Textbook Question
How would you reduce the alkene in the presence of a carboxylic acid?
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