Amines and Amides Flashcards
What is an amine?
When a hydrogen in ammonia is replaced with an organic group.
What is a primary amine?
What is a secondary amine?
What is a tertiary amine?
What is a quarternary ammonium ion ?
What are quarternary ammonium salts?
What smells do amines have?
Why can amines act as bases?
The one pair of electrons on the nitrogen can form a coordinated bond with a hydrogen ion.
What determines the strength of an amine base?
The more available the lone pair of electrons are on the nitrogen the more likely they are to form a coordinate bond with a hydrogen ion.
Why are aromatic amines the weakest type of base?
The benzene ring pulls the electrons on the nitrogen towards it meaning they are less readily available to form a coordinate bond with a hydrogen ion.
Why are aliphatic amines the strongest type of base?
The alkyl groups push the electrons on the nitrogen away from it meaning they are more readily available to form a coordinate bond with a hydrogen ion.
How strong is ammonia as a base?
It lies in the middle because it doesn’t have a benzene ring but the alkyl groups do push the pair of electrons away so they are more readily available.
What is the functional group of an amide?
Draw N-methylethanamide.
Draw N-ethylpropanamide.
Name and draw the mechanism for the reaction of bromoethane with ammonia.
Name and draw the mechanism for the reaction of bromoethane with ammonia.
Name and draw the mechanism for the reaction of bromoethane with methylamine.
How can you turn a nitrile into an amine?
You reduce it
What is the reducing agent used?
LiAlH4 and a dilute acid.
What is the use of LiAlH4 not great for industrial use?
It is too expensive.
What conditions can be used to replace the reducing agent?
- a metal catalyst like platinum and nickel
- high temperatures and pressure
When can amines act as nucleophiles?
When they react with acyl chlorides and anhydrides.
How can you make an aromatic amine?
The reduction of a nitro compound.
What happens during the reduction of nitrobenzene?
- The nitro compound, HCL and tin metal are heated under reflux to make a salt.
- Add NaOH to turn the salt to turn it into an aromatic amine.
