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|
Table of Reduction of Carboxylic Acid
Derivatives
Additions and Substitutions
(may require a hydronium workup)
| |
Net Substitutions |
Net Additions |
| Derivative (+3) |
Ketone (+2) |
Aldehyde (+1) |
Alcohol (-1) |
Amine (-1) |
|
Carboxylic Acid |
2 R-Li+ |
|
LiAlH4, 1° |
|
|
Carboxylate Salt |
R-Li+ |
|
LiAlH4, 1° |
|
|
Primary Amide |
|
[(CH3)2CHCH2]2AlH |
|
LiAlH4, 1° |
|
Secondary Amide |
|
[(CH3)2CHCH2]2AlH |
|
LiAlH4, 2° |
|
Tertiary Amide |
|
[(CH3)2CHCH2]2AlH |
|
LiAlH4, 3° |
|
Nitrile |
R-Mg++-X or R-+Li |
[(CH3)2CHCH2]2AlH |
|
LiAlH4, 1° or
H2,
transition metal catalysis |
|
Ester (not alkyl formate) |
|
[(CH3)2CHCH2]2AlH |
LiAlH4, 1° or
2R-Mg++-X, 3° |
|
|
Anhydride |
|
|
LiAlH4, 1° |
|
|
Acyl Halide |
R2Cu-Li+ |
LiAl[OC(CH3)3]3H |
LiAlH4, 1° |
|
|
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Acyl Reductions