List of Organic Reagents: I. Reducing Agents

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The document lists various organic reagents including reducing and oxidizing agents along with their reactions.

Some common reducing agents listed include lithium aluminium hydride, sodium borohydride, hydrogen gas with various catalysts and hydride reagents like DIBAL.

Some common oxidizing agents listed include selenium dioxide, periodic acid, chromium-based reagents, potassium permanganate and other metal-based oxidizing agents.

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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