Haloalkanes Mechanisms

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Chemistry

Organic Chemistry

A-Level Chemistry

AQA

Organic Chemistry

11th

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Reaction with hydroxides to form alcohols

Reagent : NaOH

Conditions : aqueous, warm

What happens : halogen atom replaced by OH group

Overall equation : CH₃CH₂Br + NaOH ➔ CH₃CH₂OH + NaBr

Mechanism : Nucleophilic Substitution

<p><strong>Reagent : </strong>NaOH</p><p><strong>Conditions : </strong>aqueous, warm</p><p><strong>What happens : </strong>halogen atom replaced by OH group</p><p><strong>Overall equation : </strong><span>CH</span><sub>3</sub><span>CH</span><sub>2</sub><span>Br + NaOH ➔ CH</span><sub>3</sub><span>CH</span><sub>2</sub><span>OH + NaBr</span></p><p><strong>Mechanism : </strong>Nucleophilic Substitution</p>

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Reaction with cyanide to form nitriles

Reagent : KCN

Conditions : aqueous ethanol, warm

What happens : halogen atom replaced by CN group

Overall equation : CH₃CH₂Br + KCN ➔ CH₃CH₂CN + KBr

Mechanism : Nucleophilic substitution

<p><strong>Reagent : </strong>KCN</p><p><strong>Conditions : </strong>aqueous ethanol, warm</p><p><strong>What happens : </strong>halogen atom replaced by CN group</p><p><strong>Overall equation : </strong><span>CH</span><sub>3</sub><span>CH</span><sub>2</sub><span>Br + KCN ➔ CH</span><sub>3</sub><span>CH</span><sub>2</sub><span>CN + KBr</span></p><p><strong>Mechanism : </strong>Nucleophilic substitution</p>

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Reaction with ammonia to form amines

Reagent : NH₃

Conditions : Excess concentrated ammonia dissolved in ethanol at pressure in a sealed container

What happens : first molecule of NH₃: halogen atom replaced by NH₃group; second molecule of NH₃: removes H⁺ from added NH₃

Overall equation : CH₃CH₂Br + 2NH₃ ➔ CH₃CH₂NH₂ + NH₄Br

Mechanism : Nucleophilic substitution

<p><strong>Reagent : </strong>NH<sub>3</sub></p><p><strong>Conditions : </strong>Excess concentrated ammonia dissolved in ethanol at pressure in a sealed container</p><p><strong>What happens : </strong>first molecule of NH<sub>3</sub>: halogen atom replaced by NH<sub>3 </sub>group; second molecule of NH<sub>3</sub>: removes H<sup>+</sup> from added NH<sub>3</sub></p><p><strong>Overall equation : </strong><span>CH</span><sub>3</sub><span>CH</span><sub>2</sub><span>Br + 2NH</span><sub>3</sub><span> ➔ CH</span><sub>3</sub><span>CH</span><sub>2</sub><span>NH</span><sub>2</sub><span> + NH</span><sub>4</sub><span>Br</span></p><p><strong>Mechanism : </strong>Nucleophilic substitution</p>

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Reaction with hydroxide to form alkenes

Reagent : KOH

Conditions : Ethanolic, hot

What happens : halogen atom and one H atom from an adjacent C atom is removed giving an alkene

Overall equation : CH₃CHICH₃ + KOH ➔ CH₂=CHCH₃ + H₂O + KI

Mechanism : Elimination

<p><strong>Reagent : </strong>KOH</p><p><strong>Conditions : </strong>Ethanolic, hot</p><p><strong>What happens : </strong>halogen atom and one H atom from an adjacent C atom is removed giving an alkene</p><p><strong>Overall equation : </strong><span>CH</span><sub>3</sub><span>CHICH</span><sub>3</sub><span> + KOH ➔ CH</span><sub>2</sub><span>=CHCH</span><sub>3</sub><span> + H</span><sub>2</sub><span>O + KI</span></p><p><strong>Mechanism : </strong>Elimination</p>