Flashcards in Amines Deck (13):
Is a primary aliphatic amine a stronger or weaker base than ammonia, and why?
Stronger, because the alkyl group pushes electrons away onto attached groups, making the nitrogen atom more electron dense, and therefore making the lone pair more available.
Is a primary aromatic amine a stronger or weaker base than ammonia, and why?
Weaker, because the bezene ring draws electrons towards itself and the nitrogen atom's lone pair of electrons gets partially delocalised onto the ring. So, the electron density on the nitrogen decreases, making the lone pair less available.
Are amines acidic or basic?
What are quaternary ammonium salts used as?
Cationic surfactants. These get rid of static and are used in things like fabric conditioners and hair products.
What type of reaction occurs when an amine or ammonia reacts with a haloalkane?
Explain the mechanism of an amine or ammonia reacting with a haloalkane.
1) The nitrogen forms a bond with the partially positively charged carbon of the C-X bond, and the halogen is released as a negative ion. The nitrogen becomes positively charged.
2) A second nitrogen atom donates its electrons to a hydrogen atom, and the electrons in the N-H bond reatreat back to the nitrogen atom.
3) The ammonium ion then reacts with the halogen to form an ammonium salt.
How can we separate primary, secondary, teritiary amines and quaternary ammonium salts?
What is the product formed when ammonia or an amine reacts with a haloalkane?
A primary aliphatic amine. Further substitution can occur to produce secondar and tertiary amines, or quaternary ammonium salts.
How can we produce a primary aliphatic amine without risk of further substitution?
By reducing a nitrile.
Give three ways in which we can reduce a nitrile.
LiAlH4 with dilute acid, or reflux with sodium metal and ethanol. Most commonly used is a nickel catalyst, hydrogen, and high pressure and temperature.
Why do we not use LiAlH4 or sodium metal to reduce nitriles in industry?
They are too expensive.
How can we produce an aromatic amine?
Reduce a nitro compound.