LIST OF ORGANIC REAGENTS

I. REDUCING AGENTS

REAGENT REACTANT PRODUCT

1. H2 in presence of
 CHO  CH2OH
metals like Ni, Pt
and Pd
 CO  CHOH
 CO2R  CH2OH
 COCl  CH2OH
 CONH2  CH2NH2
(RCO)2O RCH2OH
Lactone Diol
Epoxide Alcohol
 CN  CH2NH2

 C = NOH  CH2NH2
RNH2
RNO2
ArN = NAr
ArNO2
azo
azoxy

 C = C  CH  CH
CC  CH  CH
RX RH
ArX ArH

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REAGENT REACTANT PRODUCT

2. H2 in presence of H H
Pd partially R–CC–R C=C
R R R
deactivated by
C=O R
sulphur or Cl C=O
quinoline H
3. Hydrazine in C=O H
presence of (aldehyde or C
strong base (NH2 ketone) H
– NH2 + KOH)
Metal in liquid
NH3
4. Zinc (usually in C=O H
form of amalgam) (aldehyde or C
under acidic ketone) H
condition (usually
in HCl)
CH2SH C=O H
O (aldehyde or C
CH2SH followed ketone) H
5.
O
by Raney nickel
6. Magnesium or R R
sodium in aprotic C=O
solvent R
R C OH

R C OH

R Pinacol
7. Alkali metals in
liquid ammonia
(eg. Na in liq.
NH3)
COOH COOH

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REAGENT REACTANT PRODUCT

Alkali metals in OCH3 OCH3
liquid ammonia
(eg. Na in liq.
NH3)

8. Aluminium C=O
isopropoxide H C – OH
(aldehyde or
Al (OPri)3
ketone)
9. LiAlH4 in ether
 CHO  CH2OH
(non hydroxylic
solvent)
 CO  CHOH
 CO2R  CH2OH
 COCl  CH2OH
 CONH2  CH2NH2
(RCO)2O RCH2OH
Lactone Diol
Epoxide Alcohol
 CN  CH2NH2

 C = NOH  CH2NH2
RNH2
RNO2
ArN = NAr
ArNO2
azo
azoxy
RH
RX
ArH
ArX
C6H5 – CH2 - CH3
C6H5 – CH = CH2

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REAGENT REACTANT PRODUCT

10. LiBH4 in THF
 CHO  CH2OH
(non hydroxylic
solvent)
 CO  CHOH
 CO2R  CH2OH
 COCl  CH2OH
Lactone Diol
Epoxide Alcohol
11. NaBH4 (effective
 CHO  CH2OH
even in protic
solvent)
 CO  CHOH
RX RH

12. LiAlH4 – AlCl3

All reactants as in 9. also
reduces
 CH = CH 
CC

13. LiAlH (OtBu)3

R R
C=O C=O
Cl H

14. H – Al (iBu)2
R R
Diisobutyl C=O C=O
aluminium RO H
hydride
DIBAL – H R–CN R
C=O
H

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REAGENT REACTANT PRODUCT

15. B2H6 in THF
 CHO  CH2OH

 CO  CHOH
 CO2H  CH2OH
 CO2R  CH2OH
 CONH2  CH2NH2
(RCO)2O RCH2OH
Lactone Diol
Epoxide Alcohol

 C = C  CH  CH
CC  CH = CH 
RX RH
ArX ArH

16. 9 – B.B.N R H
C=C R – CH = CH – CH - R
(B – alkyl – 9 – C
H R |
bora bicyclo) OH
[3.3.1]nonane O

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II. OXIDIZING AGENTS :-

REAGENT REACTANT PRODUCT

O O
17. Selenium dioxide
CH3 – CH2 – C CH2 = CH - C
SeO2 in acidic or CH3 CH3
alkaline medium
(ketone) ( -  unsaturated ketone)
18. SeO2 in aqueous | | |
| | |

or alcoholic H – C|  C|  C O = C– C = C –
solution H (allylic oxidation)

19. Ceric ammonium

nitrate | | |
| | |
especially - C  C C|  OH - C  C C  O

CHO
CH3
20. CrO2Cl2 (etard’s
reagent)

R R
HO R
C=C
21. RCO3H , H3O+ H H R C-C H
H OH
(antihydroxylation)
| |

- C  O + - C= O
C OH

22. Pb(OAc)4 C OH

H
C – CH3
OH

CH3
23. NaOH – I2 _ C=O
O + CHI3

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REAGENT REACTANT PRODUCT

C OH
24. HIO4 (Periodic | |

acid) - C  O + - C= O
C OH

C OH
25. Ceric ammonimum | |
nitrate - C  O + - C= O
Ce(NH4)2(NO3)6 C OH

26. CF3CO3H in acidic O O

|| ||
medium R – C – R R – C – OR
27. B2H6 THF followed
RCH = CH2 RCH2CH2OH
by alkaline H2O2

28. Hg(OAc)2 - H2O

RCH = CH2 RCHOHCH3
followed by NaBH4

C=O
H _ C=O + Cu2O
OH O Red ppt
C
29. Benedict reagent H C=O C=O
(an alkaline R
solution containing C=O
a cupric citrate R
complex ion)

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REAGENT REACTANT PRODUCT

_ C = O + Cu2O
C=O O
30. Fehling solution Red ppt
H
(an alkaline
solution containing OH C=O
cupric tartarate C
H C=O C=O
complex ion)
R
R
_ C=O + Ag mirror
C=O O
H
31. Tollen’s reagent
OH C=O
(Ag+ complexed
with NH3) C
H C=O C=O
R
R
32. Schiff’s reagent
(Rosaniline R
hydrochloride C=O Red colour of dye is restore d
decolourized by H
SO2)
33. P.C.C (Pyridinium
chlorochromate) in R CH2OH RCHO
CH2Cl2
34. Chromic acid R R
H C - OH C=O
(H2CrO4) or H H
chromic oxide
R R
(CrO3) and K2CrO7 R C - OH C=O
in acidic medium H R
C=C C-C
-
35. KMnO4, OH (cold) –CC- OH OH
KMnO4, OH- (hot) _ + _ C=O
C=C C=O
H H O O
36. OsO4, pyridine C=C C C
followed by
Na2SO3/H2O or OH OH
NaHSO3/H2O

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REAGENT REACTANT PRODUCT

37. PCl5 R – OH R – Cl
C=O Cl
C
Cl

38. PCl3 ROH RCl

R R
C=O C=O
OH Cl
RSO2OH RSO2Cl
| | | |
39. Fe+++ – C = C – OH (– C = C – O – O)3 Fe
(Red colour)

40. N.B.S
CH2 = CH – CH3
(N bromo CH2 = CH – CH2 Br
(allylic bromination)
succinimide)

41. AlCl3 C6H6 + RCl C6H5Cl

C6H6 + ROCl C6H5COR

OCOR OH OH
COR
+

C6H6 + HCl + CO
CHO
COR

RCOOH
42. Diazo methane
C6H5OH
CH2N2
ROH
RCOOCH3
C6H5OCH3
ROCH3

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REACTANT PRODUCT
REAGENT
R R R H
43. alc. KOH H C-C H C=C
H Cl H R
(major)
R R
44. NaNH2 C=C R – C  C - R
H Cl
R
45. NaOH – Br2 C=O RNH2
H2N
46. P2O5 R
(dehydrating C=O R–CN
agent) H2N
47. conc. H2SO4
(dehydrating RCH2 CH2 OH R CH = CH2
agent)
48. Ph3P = CH2 C = CH2
(Wittig reagent) C=O

O Cl
O
49. Cl2, P CH2 C C
CH
OH OH
50. Fe2+ + H2O2 H HO
(Fenton’s reagent)

- CH(OH) – COOH - CO COOH

C OH C OH

C OH C O

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