Nucleophilic Substitution
Nucleophilic Substitution with CN- (Haloalkane → Nitrile)
Heat under reflux with an ethanolic solution of sodium cyanide / potassium cyanide.
• Can be hydrolysed to produce a carboxylic acid by heating under reflux with a strong acid.
Nucleophilic Substitution with OH- (Haloalkane → Alcohol)
Heat under reflux with warm, dilute, aqueous sodium hydroxide / potassium hydroxide.
Nucleophilic Substitution with NH3 (Haloalkane → Nitrile)
Step 1: Ammonia acts as a nucleophile and substitutes for the halogen.
Step 2: Ammonia acts as a base (a proton donator), removing a proton from the intermediate.
Heat in a sealed tube with excess ammonia dissolved in ethanol (i.e. ethanolic ammonia).
Nucleophilic Substitution with CN- (Haloalkane → Nitrile)
Heat under reflux with an ethanolic solution of sodium cyanide / potassium cyanide.
• Can be hydrolysed to produce a carboxylic acid by heating under reflux with a strong acid.
Nucleophilic Substitution with OH- (Haloalkane → Alcohol)
Heat under reflux with warm, dilute, aqueous sodium hydroxide / potassium hydroxide.
Nucleophilic Substitution with NH3 (Haloalkane → Nitrile)
Step 1: Ammonia acts as a nucleophile and substitutes for the halogen.
Step 2: Ammonia acts as a base (a proton donator), removing a proton from the intermediate.
Heat in a sealed tube with excess ammonia dissolved in ethanol (i.e. ethanolic ammonia).
