Derivatives of Carboxylic Acids - PowerPoint PPT Presentation

1 / 8
About This Presentation
Title:

Derivatives of Carboxylic Acids

Description:

Acid Halide Anhydride Ester Amide Nitrile. Esters ... N-ethyl ethanamide N, N-dimethyl methanamide. N-ethyl acetamide N, N-dimethyl formamide ... – PowerPoint PPT presentation

Number of Views:119
Avg rating:3.0/5.0
Slides: 9
Provided by: thomas358
Category:

less

Transcript and Presenter's Notes

Title: Derivatives of Carboxylic Acids


1
(No Transcript)
2
Derivatives of Carboxylic Acids Nucleophilic Acyl
Substitution
Acid Halide Anhydride Ester
Amide Nitrile
Esters
Methyl ethanoate phenyl benzoate
cyclohexyl methanoate
Methyl acetate
3
Cyclic Esters Lactones
? ? ?
H2O
?-butyrolactone
Amides
N-ethyl ethanamide N, N-dimethyl
methanamide N-ethyl acetamide N,
N-dimethyl formamide
(DMF common solvent)
4
Cyclic Amide - Lactam
? ? ?
?
?
  • - caprolactam
  • - used to make Nylon

Amides possess important resonance contributors
..
..
?



..
?
The C-N bond has partial double bond character.
Consequently, there is resistance to rotation
about the C-N bond
5
NMR spectrum of DMF
..
..
?



..
?
13C NMR 1H NMR
The two methyl groups are not equivalent due to
restricted rotation about the CN bond.
6
Anhydrides - without water
anhydride
acetic anhydride
Reactions of Carboxylic Acid Derivatives
Nucleophilic Acyl Substitution
?
?
?
7
Substrate Leaving Group
Most reactive
?
?
?
?
Least reactive
8
Reactions of Acid Chlorides
H2O
HCl
ROH
HCl
NH3
HCl
RCO2H
HCl
H-
Use LiAl(OtBu)3H
RMgX
Write a Comment
User Comments (0)
About PowerShow.com