Nitrogen organic Flashcards
Amine functional group
N bonded to 3 alkyl groups/H
Amide functional group
R-C=O bonded to N
What is an amino acid
Amine group bonded to central carbon bonded to R group bonded to carboxyl
Amine reaction with water
The lone pair on the nitrogen can accept H+
Amine reaction with acid
Lone pair on nitrogen accepts H+ and forms a salt
Amine reaction with ethanoyl chloride to form amide and salt
Reacts with cold conc. solution of amine
Nucleophilic addition of amine lone pair on d+ C.
Elimination of Cl by reformation of C=O.
Then removal of H from N by Cl (which then reacts with amine) of by amine.
Ethanoyl chloride + 2 Amine -> amide + salt
Amine reaction with halogenoalkane
Nucleophilic attack of amine lone pair onto d+ carbon on haloalkane.
Equilibrium reaction between salt formed and original amine to give secondary amine.
Can react further times to form quaternary salt.
How to prevent further reaction of amines with haloalkanes to form quaternary salts
Excess of amine - reduce the chance of haloalkane reaction with secondary amine product
Amine reacting with copper (II) ions
Cu bonded to 6 water. Amine can act as base and take 2 H+ from 2 water, creating pale blue precipitate in small amount of amine.
In excess, it can act as a ligand and replace water molecules (by forming dative covalent bonds with copper)
Why are secondary amines more basic than ammonia
The alkyl groups can donate electron density to the nitrogen, making the lone pair more electron dense and a better nucleophile
Why are aromatic amines not very basic
The lone pair on the nitrogen is incorporated into the benzene ring
Making primary amine from haloalkane
Halogenoalkane heated in conc. ethanolic ammonia in a sealed tube, creating an ammonium salt. This reacts with the ammonia to make amine and ammonium. Therefore excess amine can create primary amine. Large excess amine prevents further reaction
Making primary amines by reducing nitriles
Lithium aluminium hydride can react with nitrile in ether solvent and then treated with dilute acid (to release amine from complex ion). Then use frac dist to remove amine
CH3CN + 4[H] -> CH3CH2NH2
Preparation of phenylamine
Nitrobenzene reduced with Tin catalyst and concentrated HCl.
Preparation of amides from acyl chlorides
Conc. ammonia, sealed container
Addition elimination reaction with amine.
