REACTION MECHANISM AND KINETICS
1. Introduction to Reaction Mechanisms in Organic Chemistry
1.1. Free Radical Halogenation
Free Radical Halogenation
Example: Conversion of alkanes to alkyl halides (used in making anesthetic agents).
Proceeds via initiation, propagation, and termination steps involving radicals.
Free Radical Halogenation
Mechanism Type: Involves free radicals formed by homolytic bond cleavage; proceeds in three steps: initiation, propagation, and termination.
Example:
Methane + Cl₂ → Chloromethane (CH₃Cl) + HCl
(in the presence of UV light)
This reaction is used in the production of inhaled anesthetic agents
like halothane and chloroform.
Medical Relevance: Halogenated alkanes are starting materials for anesthetic gases.
Electrophilic Addition to Alkenes
Example: Adding HBr to ethene → bromoethane; important in pharmaceutical synthesis.
Electrophilic Addition to Alkenes
Mechanism Type: The π bond of an alkene attacks an electrophile, followed by nucleophilic addition.
Example:
Ethene + HBr → Bromoethane
CH₂=CH₂ + HBr → CH₃–CH₂Br
- Medical Relevance: Alkyl halides like bromoethane are intermediates in drug synthesis (e.g., alkylating agents in chemotherapy).
Electrophilic Aromatic Substitution (EAS)
Example: Nitration of benzene → nitrobenzene; key to creating many drugs, like painkillers.
Electrophilic Aromatic Substitution (EAS)
Mechanism Type: An electrophile replaces a hydrogen atom on an aromatic ring via formation of an arenium ion intermediate.
Example:
Benzene + HNO₃ (with H₂SO₄ catalyst) → Nitrobenzene + H₂O
Medical Relevance: Nitrobenzene is a precursor to aniline, used in making paracetamol (acetaminophen) and other analgesics.
Enzyme-Catalyzed Mechanisms
Enzymes act as biological catalysts with specific mechanisms for transforming substrates into products.
Example: Pepsin in the stomach breaks down proteins via acid-catalyzed hydrolysis.
Enzyme-Catalyzed Mechanisms
Mechanism Type: Enzymes speed up reactions by stabilizing transition states; highly specific and efficient.
Example:
Pepsin hydrolyzing proteins in the stomach
Proteins + H₂O → Peptides (via pepsin, in acidic pH)
Medical Relevance: Understanding enzyme action is key to digestive health and the design of enzyme inhibitors in drugs (e.g., protease inhibitors for HIV).