Title: Derivatives of Carboxylic Acids
1(No Transcript)
2Derivatives of Carboxylic Acids Nucleophilic Acyl
Substitution
Acid Halide Anhydride Ester
Amide Nitrile
Esters
Methyl ethanoate phenyl benzoate
cyclohexyl methanoate
Methyl acetate
3Cyclic Esters Lactones
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H2O
?-butyrolactone
Amides
N-ethyl ethanamide N, N-dimethyl
methanamide N-ethyl acetamide N,
N-dimethyl formamide
(DMF common solvent)
4Cyclic Amide - Lactam
? ? ?
?
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- - caprolactam
- - used to make Nylon
Amides possess important resonance contributors
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The C-N bond has partial double bond character.
Consequently, there is resistance to rotation
about the C-N bond
5NMR spectrum of DMF
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13C NMR 1H NMR
The two methyl groups are not equivalent due to
restricted rotation about the CN bond.
6Anhydrides - without water
anhydride
acetic anhydride
Reactions of Carboxylic Acid Derivatives
Nucleophilic Acyl Substitution
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7Substrate Leaving Group
Most reactive
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Least reactive
8Reactions of Acid Chlorides
H2O
HCl
ROH
HCl
NH3
HCl
RCO2H
HCl
H-
Use LiAl(OtBu)3H
RMgX