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Lecture notes for Organic Chemistry 2
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Complete Organic Chemistry 2 Notes, Lecture & Textbook
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12 Oxidation - ReductionDate Started @January 25, 2021
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Unit/Module Chapter 12
Week 1
12 Oxidation & Reduction
OXIDATION
- increase in number of C—Z bonds (usually C—O Bonds) or a decrease in number of C—H bonds
- decreasing electron density of carbon when adding more electronegative atom than carbon [O]
- dehydrogenation or removal of hydrogen
REDUCTION
- decrease in number of C—Z bonds (usually C—O Bonds) or an increase in number of C—H bonds
- increasing electron density of carbon when adding less electronegative atom than carbon [H]
where Z = element more electronegative than carbon
METHYL ←→ ALCOHOL ←→ ALDEHYDE ←→ CARBOXYLIC ACID
CH4 can be oxidized by replacing C—H bond with C—O bonds, and so on. Whilst, it can be reduced by replacing C—O bond with C—H bonds.
12 Oxidation - Reduction 1
, 📌 OXIDATION = adding [O] more electronegative atom than carbon atom / removing of hydrogen
REDUCTION = adding [H] less electronegative atom than carbon atom
Oxidation and Reduction of Hydrocarbons
📌 special case : two atoms are involve in a oxidation or reduction reaction net change in the number of C—H or C—Z bonds at
both atoms must be taken into account: in redox, one reaction cannot proceed without the other.
12 Oxidation - Reduction 2
, conversion of alkyne to alkene, and alkene to alkane = REDUCTION, wherein each process adds two new C—H bonds.
REDUCTION
there are three types of reduction, differing in how H2 is added.
simplest reducing agent molecular H₂
- carried out in the presence of a metal catalyst, acting as a surface where reaction occurs.
- addition is in a syn fashion
metals
Pd, Pt, Rh, or Ni are absorbed onto a finely divided inert solid, such as charcoal [C]
second way to deliver H2
- adding two protons [2H+] and two electrons [2e-] to a substrate. [H₂ = 2H + 2e]
- uses liquid ammonia (NH3) as source of protons & alkali metals as source of electrons.
third way to deliver the equivalent of two hydrogen atoms
- adding hydride [H-] and a proton [H+]
common reducing agents: contain hydrogen atom bonded to Boron or Aluminum (metal hydride reagents) — delivers hydride
to substrate & then a proton is added from H₂O or an Alcohol.
12 Oxidation - Reduction 3
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