Organic Chemistry 4e Carey
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Chapter 16: Ethers, Epoxides and Sulfides
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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
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Ethers
|
Preparations of Ethers
|
Reactions of Ethers
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Epoxides
|
Preparation of Epoxides
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Reactions of Epoxides
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Spectroscopic Analysis of Ethers
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Sulfides
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Self Assessment
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Quiz
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Spectroscopic Analysis of Ethers
Chapter 16: Ethers, Epoxides and Sulfides
Spectroscopic Analysis of Ethers
IR -
presence of C-O
Absorbance (cm-1)
Interpretation
1200 -1250 (strong, broad)
C-O stretch
1
H NMR
-
H-C-O-C
unit is the most easily recognized (similar to
H-COH
of alcohols)
Resonance (ppm)
Interpretation
3.3 - 4.0
H-C-O
(deshielding due to O)
13
C NMR
C-OH typically 57 - 87 ppm (deshielding due to O)
UV-VIS
Simple ethers give usually no absorption above 220 nm.
Mass Spectrometry
Loss of alkyl radicals due to cleavage of branches adjacent to C-O is common.
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