page 24 Flashcards
Nucleophiles and bases are structurally similar:
Both have either a lone pair or a π bond, which allows them to interact with electron-deficient sites.
Differences in Action
Bases:
Attack protons (H⁺ ions).
Involved in acid-base reactions.
Represented in the diagram by a base (B:) removing a proton (H) from the molecule.
Nucleophiles:
Attack electron-deficient atoms, typically carbons (e.g., electrophilic carbons in alkyl halides).
Involved in substitution or addition reactions.
Represented in the diagram by a nucleophile (Nu⁻) bonding with the carbon atom and displacing the leaving group.
Key Takeaways
Bases participate in proton abstraction, leaving the rest of the molecule intact.
Nucleophiles participate in forming new covalent bonds by attacking electron-deficient carbons, usually displacing leaving groups.
What do nucleophiles and bases have in common structurally?
Answer: Both have a lone pair or a π bond.
What do bases attack?
Answer: Bases attack protons (H⁺).
What do nucleophiles attack?
Answer: Nucleophiles attack electron-deficient atoms, usually carbons.
In the reaction of a base with a proton, what happens to the base?
Answer: The base forms a bond with the proton, abstracting it.
In a substitution reaction, what role does the nucleophile play?
Answer: The nucleophile replaces the leaving group by forming a covalent bond with the electrophilic carbon.
