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?
872
views
Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Mullins 1st EditionCh. 18 - Nucleophilic Acyl Substitution I: Carboxylic AcidsProblem 20b
Mullins 1st EditionCh. 18 - Nucleophilic Acyl Substitution I: Carboxylic AcidsProblem 20bChapter 17, Problem 20b
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?
Verified step by step guidance1
Understand the functional groups: Carboxylic acids contain a carbonyl group (C=O) and a hydroxyl group (O-H), while alcohols contain only a hydroxyl group (O-H).
Identify the IR spectroscopy peaks: Carboxylic acids typically show a broad O-H stretch around 2500-3300 cm-1 and a sharp C=O stretch near 1700 cm-1. Alcohols show a broad O-H stretch around 3200-3550 cm-1.
Look for the C=O stretch: The presence of a sharp peak around 1700 cm-1 in the IR spectrum indicates a carboxylic acid due to the carbonyl group.
Examine the O-H stretch: A broad peak around 2500-3300 cm-1 suggests a carboxylic acid, while a peak around 3200-3550 cm-1 suggests an alcohol.
Compare the spectra: By comparing the IR spectra of the separated compounds, you can distinguish between the carboxylic acid and alcohol based on the presence or absence of the C=O stretch and the position of the O-H stretch.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
IR Spectroscopy
Infrared (IR) spectroscopy is an analytical technique used to identify functional groups in organic compounds by measuring the absorption of infrared light, which causes molecular vibrations. Different functional groups absorb characteristic frequencies, allowing for the identification of specific bonds and structures within a molecule.
Recommended video:
Guided course
16:04
General Features of IR Spect
Carboxylic Acid Functional Group
Carboxylic acids contain a carbonyl group (C=O) and a hydroxyl group (O-H) bonded to the same carbon atom, forming the -COOH group. In IR spectroscopy, carboxylic acids show a broad O-H stretch around 2500-3300 cm⁻¹ and a sharp C=O stretch near 1700 cm⁻¹, which are key indicators of their presence.
Recommended video:
Guided course
02:36Identifying Functional Groups
Alcohol Functional Group
Alcohols are characterized by the presence of a hydroxyl group (-OH) attached to a carbon atom. In IR spectroscopy, alcohols exhibit a broad O-H stretch typically around 3200-3550 cm⁻¹. This broad peak is distinct from the carboxylic acid O-H stretch, allowing differentiation between the two functional groups.
Recommended video:
Guided course
02:36Identifying Functional Groups
Related Practice
Textbook Question
The acid-catalyzed hydrolysis of an ester results in the formation of an equal amount of carboxylic acid and alcohol.
(a) Design a flow chart for separating the two products.
1257
views
Textbook Question
Calculate the oxidation numbers for the indicated atoms.
(e)
1292
views
Textbook Question
Predict the product of the following reactions.
(a)
1128
views
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?
1011
views
Textbook Question
How would you reduce the alkene in the presence of a carboxylic acid?
1243
views