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 36
Mullins 1st EditionCh. 18 - Nucleophilic Acyl Substitution I: Carboxylic AcidsProblem 36Chapter 17, Problem 36
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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Understand the functional groups involved: Carboxylic acids have a characteristic O-H stretch in the IR spectrum, typically appearing around 2500-3000 cm-1. Acid chlorides, on the other hand, do not have this O-H stretch.
Identify the key IR band associated with carboxylic acids: The O-H stretch is a broad band due to hydrogen bonding and is a key indicator of the presence of a carboxylic acid group.
Recognize the transformation: When a carboxylic acid is converted to an acid chloride, the O-H group is replaced by a Cl atom, eliminating the O-H stretch from the IR spectrum.
Determine the absence of the band: The absence of the broad O-H stretch band in the IR spectrum of the product would indicate that the carboxylic acid has been fully converted to an acid chloride.
Conclude the analysis: By confirming the absence of the O-H stretch, you can conclude that the conversion to an acid chloride is complete, as acid chlorides will show a C=O stretch typically around 1800 cm-1 instead.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Infrared (IR) Spectroscopy
Infrared spectroscopy is a technique used to identify functional groups in a molecule by measuring the absorption of infrared light at different wavelengths. Each functional group absorbs IR light at characteristic frequencies, producing a spectrum that can be used to deduce the presence or absence of specific bonds in a compound.
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General Features of IR Spect
Carboxylic Acid Functional Group
A carboxylic acid contains a carbonyl group (C=O) and a hydroxyl group (O-H) attached to the same carbon atom. In IR spectroscopy, carboxylic acids typically show a broad O-H stretch around 2500-3300 cm⁻¹ and a sharp C=O stretch near 1700 cm⁻¹. The presence of these bands indicates the presence of a carboxylic acid group.
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Acid Chloride Functional Group
An acid chloride is derived from a carboxylic acid by replacing the hydroxyl group with a chlorine atom. In IR spectroscopy, acid chlorides show a strong C=O stretch around 1800 cm⁻¹, but lack the broad O-H stretch seen in carboxylic acids. The absence of the O-H band in the IR spectrum indicates conversion from a carboxylic acid to an acid chloride.
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Related Practice
Textbook Question
The following carboxylic acids were named incorrectly. Provide the correct name.
(b) 6-bromocyclohexane carboxylic acid
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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
How would you reduce the alkene in the presence of a carboxylic acid?
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Textbook Question
The acid-catalyzed hydrolysis of an ester results in the formation of an equal amount of carboxylic acid and alcohol.
(b) Once separated, how could you distinguish between the carboxylic acid and alcohol using IR spectroscopy?
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