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Some Oxidising Agents in Organic Chemistry
Some Oxidising Agents in Organic Chemistry
Dil. aq. alk. O3/Zn/H2O KMnO4/H+ CrO3/H+ (H2CrO4) CrO3/Anhy. Cu MnO2 Alkaline Tollen’s Fehling’s
O3/H2O PCC PDC HIO4 NaOH/I2
KMnO4 or O3/Me2S or K2Cr2O7/H+ or HNO3 e.g., pyridine at 300°C KMnO4 reagent reagent
〉C = C〈 1
C C 1
2
—CH2OH 3
4
〉CH—OH 3
5
4
6
6
C—OH 5
H
C=O
5
4
〉C = O 5
4
7
7
O
C OH
8
8
8
1. In combination with KMnO4, periodate (NaIO4) is used for oxidation of alkenes into carboxylic acids/ketones.
2. Terminal alkynes gives white ppt of silver alkynide with tollen’s reagent.
3. Allylic or benzylic alcohols are selectively oxidised into aldehydes/ketones with MnO2.
4. Ar/H/R directly attached to —CH(OH)X,—CH(OH)CH3, —COCH3, or their mono,di, tri-halogen derivatives are oxidised into corresponding carboxylic acid —COOH and CHX3.
5. >C(OH)—C(OH)< or >CO—CO< or >CH(OH)—CO— are cleaved by HIO4 into corresponding aldehydes/ketones/carboxylic acids.
6. Hemiacetals RCH(OH)(OR) are converted into parent aldehyde and hence give positive tollen’s test.
7. a-hydroxy ketones e.g. fructose give positive tollen’s test or fehling’s test.
8. Formic acid, HCOOH is oxidised by acidified KMnO4/K2Cr2O7 or tollen’s reagent/fehling’s reagent into CO2.
[O]
Ar—R Ar—COOH (R is aliphatic hydrocarbon derivative side chain having a hydrogen)
[O]
Ar—CMe3 No reaction
drastic
oxidation
Me3C—COOH
(1) CrO2Cl2/CS2
Ar—CH3 Ar—CHO (Etard reaction)
(2) H2O
(1) CrO3/Ac2O
(2) H3O+
KMnO4
R3C—H R3C—OH
–
H2O2/OH
R3B R—OH + B(OH)3
Me
O2
Ph—CHMe2 Ph—C—O—O—H
Me
O
Br2/water
—CH O — C—OH
OH O
Cr2O2–
7 /H
+
or H2CrO4
(Dark color)
O2/light
CHCl3 COCl2
–HCl
Some Reducing Agents in Organic Chemistry
–
LiAlH4 NaBH4 H2 + Catalyst H2 + Pd/BaSO4 Na + Liq. NH3 HI + Red P B2H6 DiBAL-H Zn-Hg/HCl N2H4,OH /glycol, D SnCl2/HCl Sn or Fe/HCl C2H5OH (Na)
〉C = C〈
C C
—X
—OH
H
C=O
〉C = O
O
C OH
O
C Cl — — —
O O
C O C — — —
O
C OR
— — —
C N — —
O
C NH2 — — — —
NC — — — —
NO2
+ – H3PO2 or EtOH
Ar—N2 Cl Ar—H
(—H3PO3/—CH3CHO)
Zn
Ar—OH Ar—H