Oxidation Reaction
https: Hub
General Learning Resources
Points to remember in Oxidation Reaction
(1) $\mathrm{KMnO}_{4}$ (in both medium) or $K_2 Cr_2 O_7$ (in acidic medium)
Aldehyde $\longrightarrow$ Acid
$1^{\circ}$ Alcohol $\longrightarrow$ Acid
$2^{\circ}$ Alcohol $\longrightarrow$ Ketone
$3^{\circ}$ Alcohol $\longrightarrow$ No reaction
(2) PCC (Pyridinium chlorochromate)
$CrO_{3} /HCl / Pyridine$
$1^{\circ} ROH \longrightarrow$ Aldehyde
$2^{\circ} ROH \longrightarrow$ Ketone
$3^{\circ} ROH \longrightarrow$ No reaction
(3) Cu/573 K
$1^{\circ}$ Alcohol $\longrightarrow$ Aldehyde
$2^{\circ}$ Alcohol $\longrightarrow$ Ketone
$3^{\circ}$ Alcohol $\longrightarrow$ Alkene
(4) $HIO_{4}$ (Periodic Acid):
Condition : Vicinal diol, $\alpha$ - Hydroxy ketone & $\alpha$-diketone can be oxidized by $HIO_{4}$
(5) Baeyer’s reagent and $ OsO_{4}+ NaHSO_{3}$
(6) Baeyer-Villiger oxidation (m-CPBA or $CH_{3} CO_{3} H$)
Priority of shift (O accepting aptitude)
$R^{\prime}$ = $Ph > $ Ethyl > Methyl
(7) Prilezhaev reaction
(8) Oxidation by $\mathrm{HNO}_{3}$
Aldehyde $\longrightarrow$ Acid
$1^{\circ}$ Alcohol $\longrightarrow$ Acid
$2^{\circ}$ Alcohol $\longrightarrow$ no reaction
$3^{\circ}$ Alcohol $\longrightarrow$ No reaction
(9) Oxidation by $\mathrm{MnO}_{2}$
$1^{\circ}$ Alcohol $\longrightarrow$ Aldehyde
$2^{\circ}$ Alcohol $\longrightarrow$ Ketone
$3^{\circ}$ Alcohol $\longrightarrow$ No reaction
Note : Only allylic and benzylic alcohols are oxidized by $MnO_{2}$
(10) Hydroboration Oxidation reaction
Hydroboration-oxidation is a chemical reaction widely used in organic synthesis to convert alkenes into alcohols. In the first step, an alkene reacts with borane ($BH_3$) in the presence of a solvent like tetrahydrofuran (THF). This initial step forms an organoborane intermediate by adding a $BH_2$ group across the double bond. In the second step, the organoborane undergoes oxidation with hydrogen peroxide ($H_2O_2$) and a base (such as NaOH). This oxidation replaces the boron group with a hydroxyl group (OH), resulting in the formation of an alcohol.
Oxymercuration-demercuration transforms alkenes into alcohols through a two-step process. First, the alkene reacts with mercuric acetate ($Hg(OAc)_2$) in water. The intermediate thus formed is then attacked by water to produce an organomercury compound. In the second step, reduction with sodium borohydride ($NaBH_4$) removes the mercury atom, yielding the alcohol.
(12) Ozonolysis
Ozonolysis is a chemical reaction where ozone ($O_3$) cleaves carbon-carbon double or triple bonds. This results in the formation of aldehydes, ketones, or carboxylic acids, depending on the structure of the original compound.
BETA
