SOME REDUCING AGENTS IN ORGANIC CHEMISTRY

H2/Pt or H2/Pd

alkene

alkyne

aromatic alkyl
ring
halide

alcohol

epoxide

aldehyde ketone

acid
chloride

carbox.
acid

ester

amide

nitrile

nitro,
nitroso

high P

OH

slow

slow

OH

some

H2/Pt/BaSO4

LiAlH4

CH

LiAl(OtBu)3H

NaBH4

B2H6, BH3

Na or Li

CH

Na, NH3

Sn,Zn,orFe,HCl

OH

+
+

Zn(Hg),HCl
Mg

slow

slow

RMgX

CH

OH

RLi, RNa

CH

OH

R2CuLi, R2Cd

O=C !C!

OH

RC/C!

OH

CH

CH

OH

3P=CHR
NH2NH2, OH!
alkene

+ reduction of functional group

alkyne

aromatic alkyl
ring
halide
! no reaction

alcohol

epoxide

aldehyde ketone

CH, OH acid-base reaction

OH

ester

amide

nitrile

NO2
NO

OH
+
OH
CH

OH
OH

hydrol

OH

acid
chloride

carbox.
acid

? expect reaction but no evidence found

Alkenes conjugated with carbonyls may be reduced by hydride and organometallic reagents, unlike nonpolar alkenes; C=O/C=C selectivity is always sensitive to stereochemistry
A blank space means that information was not readily available or provided examples of both + and !; contributions welcome.

L. M. SWEETING 1995