Organic Chemistry 4e Carey
Online Learning Center
Chapter 19: Carboxylic Acids
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Project Overview
How to Use This Resource
Nomenclature Quiz
Chapter 1: Chemical Bonding
Chapter 2: Alkanes
Chapter 3: Conformations of Alkanes and Cycloalkanes
Chapter 4: Alcohols and Alkyl Halides
Chapter 5: Structure and Preparation of Alkenes: Elimination Reactions
Chapter 6: Reactions of Alkenes: Addition Reactions
Chapter 7: Stereochemistry
Chapter 8: Nucleophilic Substitution
Chapter 9: Alkynes
Chapter 10: Conjugation in Alkadienes and Allylic Systems
Chapter 11: Arenes and Aromaticity
Chapter 12: Reactions of Arenes. Electrophilic Aromatic Substitution
Chapter 13: Spectroscopy
Chapter 14: Organometallic Compounds
Chapter 15: Alcohols, Diols and Thiols
Chapter 16: Ethers, Epoxides and Sulfides
Chapter 17: Aldehydes and Ketones. Nucleophilic Addition to C=O
Chapter 18: Enols and Enolates
Chapter 19: Carboxylic Acids
Chapter 20: Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution
Chapter 21: Ester Enolates
Chapter 22: Amines
Chapter 23: Aryl Halides
Chapter 24: Phenols
Summary
|
Carboxylic Acids
|
Preparations Carboxylic Acids
|
Reactions of Carboxylic Acids
|
Spectroscopic Analysis
|
Self Assessment
|
Quiz
|
Spectroscopic Analysis
Chapter 19: Carboxylic Acids
Spectroscopic Analysis
IR
- The -O-H and C=O should be obvious
Absorbance (cm
-1
)
Interpretation
2500 - 3500 (very broad)
OH stretch
1700
C=O stretch
1200-1250
C-O stretch
1
H NMR -
The -CO
2
H proton is very deshielded
Resonance (ppm)
Interpretation
10 -12 (exchangeable)
-COO
H
proton
2 - 3
H
-C-COOH
13
C NMR
C
O
2
H carbon 160 - 185 ppm (deshielded due to O, but not as much as aldehydes and ketones, 190-215 ppm)
UV-VIS
Simple carboxylic acids absorb at 210 nm, but this is too low to be particularly useful.
Mass Spectrometry
Peak for the molecular ion, M
+
, is usually prominent.
Fragments due to loss of OH (M - 17)
+
and then loss of CO (M - 45)
+
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