OXIDATION REACTION

Indah Purnama Sary

What??

FGs
undergo
??

Oxidation
reaction

Function &
Application
in Biology
and
Pharmacy??

How ??

WHAT
Oxidation: increasing the oxygen content or
decreasing the hydrogen content of an organic
molecule
A general symbol for oxidation is [O]
Oxidation can also be defined as a reaction that increases the
content of any element more electronegative than carbon

Oxidation States in Organic Chemistry

Similar to formal charges
Calculate oxidation states of C by:
-1 = a bond to H/less electronegative
+1= a bond to O, N, F, Cl, Br

Example:
Assign oxidation states to the carbon atoms of
methanol (CH3OH), formaldehyde (HCHO), and
formic acid (HCO2H), carbon dioxide (CO2) and
methane (CH4)and arrange these compounds in
order of increasing oxidation state

Oxidation Level
nn

Determine oxidation level for each

compounds above

ASSIGNMENT
Learn about:
1. FGs that undergo oxidation reaction
a. alcohol : 1, 2, 3 ???
b. alkene??
2. Mechanism of Chromate Oxidation
3. Markovnikov and Anti-Markovnikov in alkenes
4. Alcohols from Alkenes through Hydroboration
Oxidation: Anti-Markovnikov Syn Hydration

Mechanism of Chromate Oxidation

- Also called Jones oxidation
- convert 2Alcohol to Ketone

Mechanism of Chromate Oxidation

Step 1: A chromate ester is formed from the alcohol hydroxyl
Step 2: An elimination reaction occurs by removal of a hydrogen
atom from the alcohol carbon and departure of the chromium
group with a pair of electrons

Alcohols from Alkenes through HydroborationOxidation: Anti-Markovnikov Syn Hydration

The reaction leads to syn and anti-Markovnikov addition of
water to alkenes

Hydroboration: Synthesis of Alkylboranes

The elements of hydrogen and boron are added across the double bond
In practice, a borane complex with the solvent tetrahydrofuran (THF) is
often used

 Boron becomes attached to the least substituted carbon of the

double bond
The boron and hydride
add with syn stereochemistry

Oxidation and Hydrolysis of Alkylboranes

Oxidation and hydrolysis to the alcohol takes place with
retention of stereochemistry at the carbon bonded to boron