Organic Chemistry – Reaction Mechanisms & Summary
Grade
13
This lesson provides a final overview of key organic reaction mechanisms, including substitution, addition, elimination, oxidation–reduction, polymerization, and a complete summary of organic chemistry learned so far.
1. Core Concepts (Short Notes)
Organic reaction mechanisms show how and why organic reactions occur. They explain the movement of electrons, which bonds break, and which new bonds form.
Most mechanisms involve:
Movement of electron pairs (shown by curved arrows)
Attack by nucleophiles/electrophiles
Stability of intermediates
Reaction conditions (heat, catalysts, acids, bases)
2. Types of Organic Reactions
28.1 Substitution Reactions
One atom/group replaces another.
(a) Nucleophilic Substitution (SN1 & SN2)
Common in alkyl halides.
SN1: Two-step, forms carbocation, tertiary > secondary > primary.
SN2: One-step, inversion of configuration, primary > secondary > tertiary.
Examples:
R–Br + OH⁻ → R–OH + Br⁻
(b) Electrophilic Substitution (Aromatic compounds)
Benzene undergoes substitution due to delocalized ring.
Examples: nitration, halogenation, sulfonation.
Example: C₆H₆ + HNO₃ → C₆H₅NO₂ + H₂O
28.2 Addition Reactions
Typical of alkenes and alkynes.
Hydrogenation: C=C + H₂ (Ni catalyst) → alkane
Halogenation: C=C + Br₂ → dibromo compound
Hydrohalogenation: C=C + HCl → chloroalkane
Hydration: C=C + H₂O → alcohol (acid catalyst)
Markovnikov’s Rule: H attaches to carbon with more hydrogens already.
28.3 Elimination Reactions
Opposite of addition; removal of atoms/groups to form double bonds.
Example (dehydration of alcohols): CH₃CH₂OH → CH₂=CH₂ + H₂O (conc. H₂SO₄)
Example (dehydrohalogenation): R–CH₂–CH₂Br + KOH (alc.) → R–CH=CH₂ + KBr + H₂O
28.4 Oxidation & Reduction Reactions
Alcohol oxidation:
1° alcohol → aldehyde → carboxylic acid
2° alcohol → ketone
3° alcohol → no oxidation
Reduction reactions: Aldehydes/ketones → alcohols (NaBH₄)
28.5 Polymerization
Addition polymerization: Alkenes → polymers
ethene → polyethene
chloroethene → PVC
Condensation polymerization: Monomers join with loss of small molecules.
diacids + diamines → nylon
diacids + diols → polyester
3. Key Reaction Conditions
Nickel → hydrogenation
UV light → free radical substitution (alkanes + halogens)
H₂SO₄ → dehydration & addition of water
KMnO₄ → oxidation
AlCl₃/FeBr₃ → halogenation of benzene
4. Reaction Mechanism Summary Table
Reaction Type | Typical Compounds | Reagents/Conditions | Products |
Substitution | Alkyl halides | OH⁻, NH₃ | Alcohols, amines |
Electrophilic Substitution | Benzene | HNO₃, Br₂/FeBr₃ | Nitrobenzene, bromobenzene |
Addition | Alkenes | H₂, Br₂, HCl, H₂O | Alkanes, dihalides, alcohols |
Elimination | Alcohols, haloalkanes | Heat, H₂SO₄, KOH (alc.) | Alkenes |
Oxidation | Alcohols, aldehydes | KMnO₄, K₂Cr₂O₇ | Acids, ketones |
Reduction | Carbonyls | NaBH₄ | Alcohols |
Polymerization | Alkenes, monomers | Catalysts, heat | Polymers |
5. Tips & Tricks for Exams
Always identify functional groups first—the mechanism depends on them.
Use Markovnikov’s rule for addition to asymmetrical alkenes.
Memorize color changes of oxidizing agents (e.g., orange → green for dichromate).
SN1 gives racemic mixtures; SN2 gives inversion (important exam point).
For benzene reactions, always use substitution (not addition).
In mechanism questions, draw curved arrows to show electron movement.
6. Final Organic Chemistry Summary
Key Families & Their Reactions
Alkanes: substitution, combustion
Alkenes/Alkynes: addition, polymerization
Alcohols: oxidation, dehydration, substitution
Aldehydes/Ketones: oxidation, reduction, nucleophilic addition
Carboxylic acids: neutralization, esterification
Esters: hydrolysis
Amines: basic reactions, substitution
Benzene: electrophilic substitution
Essential Skills
Recognizing mechanisms
Predicting products
Writing structural formulas
Understanding electron flow
Applying reagent conditions correctly
7. Important Points to Remember
Mechanisms explain how reactions occur.
Reaction conditions dramatically influence products.
Functional groups determine reactivity.
Stability of intermediates affects pathway (SN1 vs SN2).
Organic chemistry builds progressively—each lesson connects to the next.
වියාචනය (Disclaimer)
Idasara Academy ඉගෙනුම් සම්පත් නිර්මාණය කර ඇත්තේ සිසුන්ට මගපෙන්වීම, පුහුණුව සහ අධ්යයන උපායමාර්ග ලබාදී සහයෝගය දැක්වීමටය.
කෙසේ වෙතත්, සියලුම විභාග සහ නිල අවශ්යතා සඳහා, සිසුන් අනිවාර්යයෙන්ම ශ්රී ලංකා අධ්යාපන අමාත්යාංශයේ, අධ්යාපන ප්රකාශන දෙපාර්තමේන්තුව විසින් ප්රකාශයට පත් කරන ලද නිල පෙළපොත් සහ සම්පත් පරිශීලනය කළ යුතුය.
ජාතික විභාග සඳහා අන්තර්ගතයේ නිල බලය ලත් මූලාශ්රය වනුයේ රජය විසින් නිකුත් කරනු ලබන මෙම ප්රකාශනයි.
