Reactivity 3. What are the mechanisms of chemical change? - Electron sharing reactions
Review the key concepts, formulae, and examples before starting your quiz.
🔑Concepts
Bond Fission: Chemical reactions involve the breaking of covalent bonds. This can occur via homolytic fission, where each atom retains one electron from the shared pair, forming radicals (), or heterolytic fission, where one atom retains both electrons, forming ions ( and ).
Lewis Acids and Bases: A Lewis acid is an electron pair acceptor (e.g., , , or ), while a Lewis base is an electron pair donor (e.g., , , or ).
Nucleophiles and Electrophiles: Nucleophiles () are electron-rich species with a lone pair that seek electron-deficient centers. Electrophiles () are electron-deficient species that seek electron-rich centers like double bonds.
Curly Arrow Notation: Double-headed curly arrows represent the movement of an electron pair (). Single-headed 'fishhook' arrows represent the movement of a single electron ().
Radical Substitution: Occurs in alkanes (e.g., with or in UV light). It involves three stages: Initiation (homolytic fission), Propagation (regeneration of radicals), and Termination (combination of radicals).
Nucleophilic Substitution ( and ): Mechanisms for the reaction of haloalkanes. is a concerted one-step process favored by primary haloalkanes, while is a two-step process involving a carbocation intermediate (), favored by tertiary haloalkanes.
Electrophilic Addition: The characteristic reaction of alkenes. The high electron density of the bond attracts electrophiles (e.g., or ), leading to the addition of atoms across the double bond.
📐Formulae
💡Examples
Problem 1:
Describe the initiation step for the reaction between methane () and chlorine () in the presence of ultraviolet (UV) light.
Solution:
Explanation:
The UV light provides the necessary energy to break the covalent bond homolytically. Each chlorine atom takes one electron from the shared pair, resulting in the formation of two highly reactive chlorine radicals.
Problem 2:
Identify the Lewis acid and Lewis base in the reaction:
Solution:
Lewis Acid: ; Lewis Base:
Explanation:
Boron trifluoride () has an incomplete octet and accepts an electron pair from the nitrogen atom in ammonia (). Since accepts the pair, it is the Lewis acid, and is the Lewis base (donor).
Problem 3:
Outline the mechanism for the reaction between chloromethane () and hydroxide ions ().
Solution:
Explanation:
The nucleophile () attacks the electron-deficient carbon atom from the opposite side of the leaving group (). A transition state is formed where the bond is partially formed and the bond is partially broken. This is a one-step bimolecular process.