|
Table of Reduction of Carboxylic Acid
Derivatives
Additions and Substitutions
(may require a hydronium workup)
(The links on this page lead to "pencast"
presentations of the mechanism of each reaction!)
| |
Net Substitutions |
Net Additions |
| Derivative (+3) |
Ketone (+2) |
Aldehyde (+1) |
Alcohol (-1) |
Amine (-1) |
| Carboxylic Acid |
|
|
LiAlH4, 1° |
|
| Carboxylate Salt |
|
|
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° |
|
| |
|
Acyl Reductive Addition