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21- Carboxylic Acid Derivatives

21- Carboxylic Acid Derivatives

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Published by: Elizabeth Jean Baumeister on May 01, 2011
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Chapter 21: Carboxylic Acid Derivatives
Start with:Use:Product:Notes
HydrolysiscarboxylicderivativeH
+
or
-
OHcarboxylic acidamides and nitriles requirestronger conditions (heat)TransesterificationesterR''-OH (excess)/H
+
or
-
OR''different esteracid/acidchloride/esterLiAlH
4
1
o
alcoholaldehyde intermediateacid chlorideLi(
-BuO)
3
AlH /etheraldehydeamide1) LiAlH
4
2) H
2
OamineGrignard Additionester/acidchloride1) 2 R''-MgX2) H
3
O
+
3
o
alcoholalkoxide salt intermediateH
2
Ocarboxylic acidR-'OHesterR'-NH
2
amideR'-COOHanhydride1) LiAlH
4
2) H
2
O1
o
alcohol1) 2 R'MgX 2) H
2
O3
o
alcoholR
2
CuLiketoneReductionacid chlorideReactions of AcidChlorides
 
Chapter 21: Carboxylic Acid Derivatives
Li(
-BuO)
3
AlH /etheraldehydeactivated benzeneacylbenzeneSynthesis of Anhydridescarboxylic acidacid chlorideacid anhydrideH
2
Ocarboxylic acidR'OH/H
+
esterR'NH
2
amidecarboxylicacid/acidchloride/anhydride/esterR'OH/H
+
estercarboxylic acidCH
2
N
2
methyl esterH
2
O/H
+
or
-
OHcarboxylic acid +alcoholR''OH/H
+
or
-
OR''different ester +alcoholtransesterificationR''NH
2
amide + alcohol1) LiAlH
4
2) H
2
O1
o
alcohol +alcoholSynthesis of EstersReactions of Estersester anhydride Reactions of Anhydrides
 
Chapter 21: Carboxylic Acid Derivatives
1) 2 R''MgX2) H
2
O3
o
alcohol +alcoholLactone Formationhydroxy acidH
+
lactonedistilling out the water formeddrives the reaction pastequilibriumcarboxylic acidR'NH
2
(300
o
C)amideacid chloride2 R'
2
NHamideanhydrideR'
2
NHamide +carboxylic acidesterR'NH
2
amide + alcoholnitrileH
2
O/H
+
or
-
OH1
o
amideH
2
O/H
+
or
-
OHcarboxylic acid1) LiAlH
4
2) H
2
OamineBr
2
,
-
OH1
o
amineHoffmann RearangementPOCl
3
nitrileFormation of Lactamsamino acidheatlactam1
o
amidePOCl
3
nitrileReactions of Amides1
o
amideamide Synthesis of Amides

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