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Oxidation reaction involving
N-bromosuccinimide
&
Hydrogen peroxide
Oxidation
Its is defined as
addition of oxygen
removal of electron
removal of hydrogen
Oxidation reaction involving N-bromosuccinimide
Oxidation of primary alcohol
Oxidation of primary alcohol by N-bromosuccinimide
gives primary aldehyde .
R-CH2-OH R-CHO + HBr +
N-bromosuccinimide (NBS)
NBS
Mechanism
1) The lone pair of oxygen in alcohol attack a nitrogen
in oxidizing reagent (NBS)
H
R C OH +
H H
C R
H
H
+
2) Removal of HBr
H H
C R
H
+
H
C R
H
- HBr
3) Rearrangement and formation of aldehyde
H
C R
H Rearrangement
+
R C O
H
succinimide
aldehyde
Oxidation reaction involving Hydrogen
peroxide
Carboxy acids on treatment with hydrogen
peroxide are converted into per acids .
R C OH R C O OH
O O
H2O2
Carboxy acid per acid
some mineral acid is added as a catalyst .
Mechanism
1) Protonation
Carboxy acid is protonated , proton from mineral
acid.
O O H
R C OH R C OH
2) Action of H2O2 and formation of leaving group .
O H OH
R C OH R C OH
H O O H
+
H+H+H+
H+
+
H -O -O - H
+
OH H
R C O H
O O H
3) Removal of water and proton.
OH H OH
R C O H R C O O H
O O H
O
R C O O H
+
+ - H2O
+ - H+
per acid
Oxidation of aromatic carbonyl
compound
An aromatic aldehyde or ketone containing
hydroxy or amino group in ortho or para position is
converted into phenol .
H2O2
Quinol
P-hydroxyacetophenone
NaOH
CH3
Mechanism
1) Nucleophile attack the hydrogen peroxide .
H2O2 + OH H2O + OOH
2)
- -
+ OOH
-CH3
C CH3
O
OOH
-
3) Rearrangement and hydrolysis
O
CH3
O – O – H
C
-
Rearrangement
-OH
-
O C= O
CH3
hydrolysis
Quinol
CH3COOH +
Application
1) It finds use in medicine as an antiseptic for washing
wounds , teeth , ears .
2) As an oxidizing agent in laboratory due to its
tendency to lose one atom of oxygen
3) For bleaching hair , straw , silk , wool and ivory .
4) As a propellant or fuel in submarines and rockers .
5) It is also act as a reducing agent because when
brought in contact with other oxidizing agents , one
atom of nascent oxygen from each forms a
molecule of oxygen
e.g
potassium permanganate is reduced in acidic
medium .
2KMnO4 + 2H2SO4 + 5H2O2 K2SO4 +
2MnSO4 + 8H2O + 5O2
Stereochemistry aspects

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oxidation reaction mechanism by reagent n-bromosuccinimide,hydrogen peroxide reaction and mechanism

  • 2. Oxidation Its is defined as addition of oxygen removal of electron removal of hydrogen
  • 3. Oxidation reaction involving N-bromosuccinimide Oxidation of primary alcohol Oxidation of primary alcohol by N-bromosuccinimide gives primary aldehyde . R-CH2-OH R-CHO + HBr + N-bromosuccinimide (NBS) NBS
  • 4. Mechanism 1) The lone pair of oxygen in alcohol attack a nitrogen in oxidizing reagent (NBS) H R C OH + H H C R H H +
  • 5. 2) Removal of HBr H H C R H + H C R H - HBr 3) Rearrangement and formation of aldehyde
  • 6. H C R H Rearrangement + R C O H succinimide aldehyde
  • 7. Oxidation reaction involving Hydrogen peroxide Carboxy acids on treatment with hydrogen peroxide are converted into per acids . R C OH R C O OH O O H2O2 Carboxy acid per acid some mineral acid is added as a catalyst .
  • 8. Mechanism 1) Protonation Carboxy acid is protonated , proton from mineral acid. O O H R C OH R C OH 2) Action of H2O2 and formation of leaving group . O H OH R C OH R C OH H O O H + H+H+H+ H+ + H -O -O - H +
  • 9. OH H R C O H O O H 3) Removal of water and proton. OH H OH R C O H R C O O H O O H O R C O O H + + - H2O + - H+ per acid
  • 10. Oxidation of aromatic carbonyl compound An aromatic aldehyde or ketone containing hydroxy or amino group in ortho or para position is converted into phenol . H2O2 Quinol P-hydroxyacetophenone NaOH CH3
  • 11. Mechanism 1) Nucleophile attack the hydrogen peroxide . H2O2 + OH H2O + OOH 2) - - + OOH -CH3 C CH3 O OOH -
  • 12. 3) Rearrangement and hydrolysis O CH3 O – O – H C - Rearrangement -OH - O C= O CH3 hydrolysis Quinol CH3COOH +
  • 13. Application 1) It finds use in medicine as an antiseptic for washing wounds , teeth , ears . 2) As an oxidizing agent in laboratory due to its tendency to lose one atom of oxygen 3) For bleaching hair , straw , silk , wool and ivory . 4) As a propellant or fuel in submarines and rockers . 5) It is also act as a reducing agent because when brought in contact with other oxidizing agents , one atom of nascent oxygen from each forms a molecule of oxygen
  • 14. e.g potassium permanganate is reduced in acidic medium . 2KMnO4 + 2H2SO4 + 5H2O2 K2SO4 + 2MnSO4 + 8H2O + 5O2