Haloalkanes Mechanisms

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1
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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&nbsp;➔ CH</span><sub>3</sub><span>CH</span><sub>2</sub><span>OH + NaBr</span></p><p><strong>Mechanism : </strong>Nucleophilic Substitution</p>
2
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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&nbsp;➔ CH</span><sub>3</sub><span>CH</span><sub>2</sub><span>CN + KBr</span></p><p><strong>Mechanism : </strong>Nucleophilic substitution</p>
3
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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

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>Overall equation : </strong><span>CH</span><sub>3</sub><span>CH</span><sub>2</sub><span>Br + 2NH</span><sub>3</sub><span>&nbsp;➔ 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>
4
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Reaction with hydroxide to form alkenes

Reagent : KOH

Conditions : Ethanolic, hot

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>Overall equation : </strong><span>CH</span><sub>3</sub><span>CHICH</span><sub>3</sub><span> + KOH&nbsp;➔ 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>

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