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® Reduction

REDUCTION
REDUCING AGENTS AND THEIR ROLE

Group Product LAH in NaBH4 B2H6 H2 /

Ether in H2O in THF Catalyst Χ

–CHO –CH2OH + + + +

>C = O >CH – OH + + + +

–CO2H –CH2OH + – + –

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–CO2R –CH2OH + – + +

–COCl –CH2OH + + – +

–CONH2 –CH2NH2 + – + +

(RCO)2O RCH2OH + – + +

–CN –CH2NH2 + – + +
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>C = NOH –CH2NH2 + – – +

>C = C< >CH – CH< – – + +

–C ≠ C– –CH = CH– – – + +

1° RX RH + – – +

Note :
1. B2H6 in THF not able to reduce cyclic ester.

2. NaBH4 can also reduce imine group ( C = NH ).

3. Reactivity order towards Ni / H2 , Χ ⇑ –C ≠ N > –C – O – R

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JEE-Chemistry ≅ΚΚ∆Μ
®

Name Reagent Function

H
Wolf Kishner Reduction (i) N2H4 / (ii) KOH, O
H
H
Clemenson Reduction Zn–Hg / HCl O
H
SH H
Mozingo Reduction Dry HCl, followed
O
by Raney Ni
SH H
SnCl2 / HCl followed
Stephen's Reduction + R–C N R–CH=O
by H3O
CH3

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CH3
MPV Reduction Al –O–CH HO–CH O OH
CH3 3 CH3

C=C C—C
H H
Hydroboration Reduction B2H6 / AcOH, H2O
O O
H H

Bouvoult Blank Reduction Na / EtOH R–COO–R RCH2OH +ROH

Transfer Hydrogenation N2H4 / H2O2 C=C C—C

H H
O O

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H2, Pd–BaSO4 R—C—Cl R—C—H
Rosenmund Reduction
* —C C— —C C—
H H
H
Birch Reduction Na / Liq. NH3 —C C— —C C—
H
—COOR
H–Al –CH2–CH–CH3 —C N
CH3 2 —COCl —CHO
DIBAL-H O O
(–78°C) followed by H3O+ —C–O–C–

—CHO —CH2OH

R–CO2H RCH3
R–CH=O RCH3
Red phosphorus in R–C–R RCH2R
presence of HI Red P + HI
O
R–OH R–H
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