Hydride Reductions

Hydride Reduction

1) NaBH4/EtOH

or

2) LiAlH4/ether/H3O+

-aldehyde and ketone reactants yield ____

-carbonyl reduction cant produce ___

- primary and secondary alcohols

- tertiary alcohols

NaBH4 vs LiAlH4

- NaBH4 can reduce aldehydes, ketones

- LAH (more powerful) can reduce aldehydes, ketones, esters, and carboxylic acids

Reduction of an Aldehyde to a ___

1 ̊Alcohol

Reduction of a Ketone to a ___

2 ̊Alcohol

Reduction of a Carboxylic Acid to a ___

1 ̊Alcohol

Reduction of an Ester to a ___ Alcohol

1 ̊Alcohol

Reduction of an Ester to an Aldehyde

DIBAL-H

Reduction of an Acyl Chloride to a __ Alcohol

1 ̊Alcohol

Reduction of an Acyl Chloride to an Aldehyde

Reduction of an Amide to an ___

Amine

Hofmann Rearrangement

1 ̊ amide -> 1 ̊ amine with one fewer carbon atom

1) Br2

2) NaOH

Reduction of a Nitrile to an ____

Amine