Textbook Question
At the end of a reduction, there was found to be a small amount of unreacted amide along with the amine product dissolved in diethyl ether. How might you remove the amine from the ether?
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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 49b
Mullins 1st EditionCh. 18 - Nucleophilic Acyl Substitution I: Carboxylic AcidsProblem 49bChapter 17, Problem 49b
The following carboxylic acids were named incorrectly. Provide the correct name.
(b) 6-bromocyclohexane carboxylic acid
Verified step by step guidance1
Identify the structure of the compound: The name '6-bromocyclohexane carboxylic acid' suggests a cyclohexane ring with a bromine substituent and a carboxylic acid group.
Understand the numbering of the cyclohexane ring: In cyclohexane, the numbering starts from the carbon attached to the functional group, which is the carboxylic acid group in this case.
Locate the substituent: The bromine substituent should be correctly numbered based on its position relative to the carboxylic acid group. Since cyclohexane is a ring, the numbering should start from the carbon attached to the carboxylic acid group.
Correct the numbering: Ensure that the bromine is at the lowest possible number. In a cyclohexane ring, the carboxylic acid group is at position 1, so the bromine should be numbered accordingly.
Provide the correct name: Based on the correct numbering, the name should reflect the position of the bromine substituent relative to the carboxylic acid group, ensuring the lowest possible number for the substituent.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
IUPAC Nomenclature
The International Union of Pure and Applied Chemistry (IUPAC) nomenclature is a standardized method for naming chemical compounds. It ensures that each compound has a unique and universally accepted name. For carboxylic acids, the name is derived from the longest carbon chain containing the carboxyl group, with the suffix '-oic acid' added. Substituents are named and numbered according to their position on the chain.
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The different parts of an IUPAC name
Cycloalkane Naming
Cycloalkanes are saturated hydrocarbons with carbon atoms arranged in a ring. When naming cycloalkanes, the prefix 'cyclo-' is added to the alkane name corresponding to the number of carbon atoms in the ring. Substituents on the ring are named and numbered to give the lowest possible numbers, and the carboxyl group takes priority in numbering.
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Functional Group Priority
In organic chemistry, functional groups are specific groups of atoms within molecules that determine the chemical properties of those molecules. The carboxyl group (-COOH) is one of the highest priority functional groups. When naming compounds, the carboxyl group is given the highest priority, influencing the numbering of the carbon chain and the naming of the compound.
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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
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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Textbook Question
How would you reduce the alkene in the presence of a carboxylic acid?
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