3.3 Halogenoalkanes
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General formula of halogenoalkanes
CₙH₂ₙX (X = F,Cl, Br, I)
Functional group of halogeoalkanes
C-X
Why are halogenoalkanes more reactive than alkanes?
They have a polar bond
Uses of halogenoalkanes
• Refrigerants • Solvents • Pharmaceuticals
What order are halogens named in a halogenoalkane
Alphabetical order
Nucleophile
An electron pair donator
Why do halogenoalkanes have nucleophilic substitution reactions?
They have a polar carbon-halogen bond
What happens in a nucleophilic substitution reaction?
• Nucleophile donates electron pair to the δ+C atom • This forms a new colvalent bond • The C-X bond breaks • Halide ion is formed
Product of the reaction between halogenoalkanes and aqueous hydroxides
Alcohols
What type of reaction is halogenoalkane + aqueous hydroxide?
Hydrolysis (the mechanism is nucleophilic substitution)
Conditions for hydrolysis of halogenoalkanes with aqueous hydroxides
• Warm • Aqueous
Reagent for hydrolysis of halogenoalkanes with aqueous hydroxides
NaOH / KOH
General equation for hydrolysis of halogenoalkanes
RX + NaOH → ROH + NaX R - hydrocarbon chain X - halogen
Ethanolic
Solution in ethanol
Product of the reaction between halogenoalkanes and potassium cyanide
Nitriles
Conditions for the reaction between halogenoalkanes and potassium cyanide
• Warm • Ethanolic
Nitrile group
C≡N
General equation for the reaction between halogenoalkanes and potassium cyanide
RX + KCN → RCN + KX R - hydrocarbon chain X - halogen
What effect does reacting halogenoalkanes with cyanide have on the carbon chain?
Increases the chain length
Mechanism for halogenoalkane + potassium cyanide
Nucleophilic substitution
Mechanism for halogenoalkane + ammonia
Nucleophilic substitution
Halogenoalkanes are reacted with ______ ammonia to form ______
Excess, amines
Reagent for forming amines from halogenoalkanes
Excess ammonia
Conditions for nucleophilic substitution of halogenoalkanes + ammonia
• Warm • Sealed tube • Ethanolic