Nucleophilic Properties of Amines
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Why can ammonia act as a nucleophile? (lp. e - don. elec. def. crbn. atm.)
It has a lone pair of electrons that can donate to an electron deficient carbon atom
Why is excess ammonia used when preparing amines from halogenoalkanes? (red. chnces. - amine rct. frthr. w/ halgnalk.)
It reduces the chances of the newly formed amine reacting further with the halogenoalkane
Which substances can undergo nucleophilic substitution with halogenoalkanes?
Ammonia and primary, secondary, and tertiary amines can all undergo nucleophilic substitution
Outline the nucleophilic substitution that takes place between bromoethane and ammonia to produce a primary amine. Name the product
Ethylamine
Outline the nucleophilic substitution that takes place between bromoethane and ethylamine to produce a secondary amine
diethylamine
Outline the nucleophilic substitution that takes place between bromoethane and diethylamine to produce a tertiary amine
Triethylamine
What happens when excess halogenoalkane is used in the reaction?
The likelihood of further reactions increases, leading to the formation of more substituted amines
Name this compound
Quaternary ammonium ion
What is a key use of quaternary ammonium salts?
They are used as cationic surfactants
Phenylamine reacts with butanoyl chloride to form an amide and a salt Draw the complete mechanism
N - phenylbutanamide