Amines Flashcards
Preparation of amines
When 1 or more of the hydrogennatomsnin ammonia is replaced with an organic group.
Amine production from nucleophilic substitution
Reaction of haloalkanes and ammonia in a sealed tube. 1 mole of haloalkane reacts with 2 makes of ammonia producing a primary amine and an ammonium salt. Substitution can continue until all the hydrogen atoms have been replaced with organic groups. Following this, an additional substitution can occur producing a quaternary ammonium salt.
Reduction of nitriles
Reducing nitrites via hydrogenation can produce Amines. Requires LiAlH⁴ (reducing agent) and acidic conditions or a combination of hydrogen and a nickel catalyst.
Aromatic amine production
Produced from the reduction of nitrobenzene (benzene with NO² instead of a H) using conc HCl and a Tin catalyst.
Amine properties
Weak bases because the lone electron pair on the N atom can accept protons. The base strength of an amine depends on how available the electron pair is.
What is the inductive effect
Where functional groups affect how available a lone electron pair is by changing electron density around the bond.
What inductive effect does benzene have
Draws electrons away making it less available
What inductive effect do alkyl groups have
Push electron density towards the nitrogen making it more available. More alkyl groups leads to more pushing.