Learning objective

Explain the role of hydroxide ions as nucleophile and base.

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Topic

Halogenoalkanes

Subtopic

Elimination

AQA A Level ChemistryOrganic chemistry

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Short explanation

In an E2 elimination, the hydroxide ion (OH⁻) acts simultaneously as a strong base and a good nucleophile. The base component abstracts a β‑hydrogen from the halogenoalkane, forming a C=C double bond, while the nucleophilic part donates its lone pair to the electron‑poor carbon bearing the leaving halogen, facilitating C–X bond cleavage. This concerted mechanism requires a strong base to deprotonate and a nucleophile capable of stabilising the transition state, which explains why OH⁻ is effective in E2 reactions. The dual role of OH⁻ ensures both proton removal and halogen departure occur in a single step, leading to efficient alkene formation.

Key concepts

hydroxide ionnucleophile

Why it matters

This objective helps connect Elimination to exam-style questions, flashcards, and revision notes for Halogenoalkanes.

Common mistakes

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  • Misunderstanding Hydroxide Ion Roles: To clarify, hydroxide ions (OH-) can act as nucleophiles in nucleophilic substitution reactions by attacking electrophilic carbon atoms, and as bases in elimination reactions by abstracting protons. Always specify the context of the reaction to determine their role. For example, in a reaction with a halogenoalkane, state that OH- acts as a nucleophile when substituting the halogen and as a base when facilitating elimination.

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Explain the role of hydroxide ions as nucleophile and base. |… | ExamCompanion