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21- Carboxylic Acid Derivatives
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21- Carboxylic Acid Derivatives
Reactions for Chapter 21: Carboxylic Acid Derivatives...
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Elizabeth Jean Baumeister
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Chapter 21: Carboxylic Acid Derivatives Start with:
Use:
Hydrolysis
carboxylic derivative
H or OH
Transesterification
ester acid/acid chloride/ester
Reduction
Grignard Addition
Reactions of Acid Chlorides
acid chloride
+
-
R''-OH (excess)/ +
-
H or OR'' LiAlH4 Li(t -BuO) -BuO)3AlH /ether
amide
1) LiAlH4 2) H2O
ester/acid chloride
1) 2 R''-MgX +
2) H3O
Product:
Notes
carboxylic acid
amides and nitriles require stronger conditions (heat)
different ester o
1 alcohol aldehyde amine o
3 alcohol
H2O
carboxylic acid
R-'OH
ester
R'-NH2
amide
R'-COOH
anhydride
1) LiAlH4 2) H2O
1 alcohol
1) 2 R'MgX 2) H2O
3 alcohol
R2CuLi
ketone
acid chloride
aldehyde intermediate
o
o
alkoxide salt intermediate
Chapter 21: Carboxylic Acid Derivatives Li(t -BuO) -BuO)3AlH /ether
Synthesis of Anhydrides
Reactions of Anhydrides
carboxylic ac acid
anhydride
carboxylic acid/acid chloride/anhydrid Synthesis of Esters e/ester carboxylic acid
Reactions of Esters
ester
aldehyde
acti activ vate ated be benzen nzene e
acy acylbe lbenzen nzene e
acid ch chloride
acid an anhydride
H2O
carboxylic acid
R'OH/H
ester
R'NH 2
amide
+
+
R'OH/H
ester
CH2N2
methyl ester
H2O/H or OH
+
-
carboxylic acid + alcohol
R''OH/H or OR''
+
-
different ester + alcohol
R''NH2
amide + alcohol
1) LiAlH4 2) H2O
1 alcohol + alcohol
o
transesterification
Chapter 21: Carboxylic Acid Derivatives 1) 2 R''MgX 2) H2O Lac Lacton tone Forma ormati tion on
o
3 alcohol + alcohol
hydro droxy acid acid
H
lactone
carboxylic acid
R'NH2 (300 C)
amide
acid chloride
2 R'2NH
amide
anhydride
R'2NH
amide + carboxylic acid
ester
R'NH2
amide + alcohol
nitrile
H2O/H or OH
+
o
Synthesis of Amides
amide
+
-
+
-
distilling out the water formed drives the reaction past equilibrium
o
1 amide
H2O/H or OH
carboxylic acid
1) LiAlH4 2) H2O
amine
Reactions of Amides -
o
1 amide Formation of Lactams
amino acid o
1 amide
o
Br2, OH
1 amine
POCl3
nitrile
heat
lactam
POCl3
nitrile
Hoffmann Rearangement Rearangement
Chapter 21: Carboxylic Acid Derivatives Synthesis of Nitriles
alkyl halide
NaCN
nitrile
diazonium salt (Ar-NN)
CuCN
aryl nitrile
ketone/aldehyde
HCN/KCN
cyanohydrin
H2O/H or OH
amide, then carboxylic acid (with heat)
1) LiAlH4 2) H2O
amine
+
Reactions of of Ni Nitriles
nitrile
-
+
Thioester Formation
carboxylic acid
1) R'MgX 2) H3O
ketone
R'SH
thioester
imine salt intermediate
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