AC13: Organic N Compounds Flashcards
What is an amine
A compound with NH or NH2 or N as its functional group
What are the differences between a primary, secondary, and tertiary amine
primary amine has NH2 - N is bonded to one alkyl chain
secondary amine has NH - N is bonded to two alkyl chains
tertiary amine has N - N is bonded to three alkyl chains
What does ethanolic mean
dissolved in ethanol
How do you prepare aliphatic primary amines
Haloalkane (chloroalkane) + ammonia and (heat with excess ethanolic ammonia) -> primary amine + hydrogen halide (HCl)
What is the mechanism for preparing amines and explain it
Nucleophilic substitution
curly arrow from lone pair on N to the delta positive on the haloalkane. Curly arrow from delta positive carbon to halogen. Forms amine with positive charge on N and a chloride ion. Add OH- to deprotonate the organic product to form the free amine
How do you prepare aliphatic secondary and tertiary amines
Add excess primary amine in ethanolic solution to a chloroalkane and heat to give a desirable yield of secondary amine. Tertiary amines are formed from further substitution of secondary amines therefore use secondary amines.
How do you prepare aromatic amines
benzene + nitric acid (50 degrees celsius, conc HNO3, conc H2SO4) -> nitrobenzene + water
nitrobenzene + 6 [H] ( Sn/conc HCl, heat under reflux) -> aromatic amine + 2 H2O
How do you prepare amines fro nitriles and how is this useful
nitrile + 2H2 (Ni/Pt catalyst and heat) -> amine
useful reaction to extend the carbon chain
What makes an amino acid, an alpha amino acid
The two functional groups are bonded to the “alpha carbon” (2nd carbon)
What is an amide
A compound with a N-C=O functional group
What are the differences between a primary, secondary, and tertiary amide
primary amide has NH2 - N is bonded to one alkyl chain
secondary amide has NH - N is bonded to two alkyl chains
tertiary amide has N - N is bonded to three alkyl chains
How do you prepare primary amides
Acyl chloride + ammonia (excess ethanolic ammonia) -> amide + ammonium chloride
How do you prepare secondary amides
Acyl chloride + primary amine (excess ethanolic primary amine) -> amide + NH3Cl (bonded to alkyl group from primary amine)
How do you prepare tertiary amides
Acyl chloride + secondary amine (excess ethanolic secondary amine) -> amide + NH2Cl (bonded to the two alkyl groups from secondary amine)
What is a nitrile
a compound with a CN functional group (C triple bond N)
State 2 ways to prepare nitriles
from carbonyls or from haloalkanes
How do you prepare nitriles from carbonyls
aldehyde/ketone + HCN (NaCN + conc sulfuric acid) -> nitrile (the double bonded O is now -OH)
Explain the mechanism nitriles are prepared from carbonyls
Nucleophilic addition
curly arrow from :CN- ion to partial positive charge on central C
curly arrow from double bond (C=O) to O
curly arrow from :O- to H+
forms nitrile with hydroxyl group
How do you prepare nitriles from haloalkanes
haloalkane + CN- (NaCN + ethanolic solution) -> nitrile + halide ion
Explain the mechanism nitriles are prepared from haloalkanes
Nucleophilic substitution
curly arrow from :CN- ion to partial positive charge on C bonded to halogen
curly arrow from bond (C-halogen) to halogen
forms nitrile and halide ion
How can you reduce nitriles and what is produced
nitrile + 2H2 (Ni/Pt catalyst and heat) -> amine
How can you hydrolyse nitriles and what is produced
nitrile + 2H2O + HCl (heat and aqueous HCl) -> Carboxylic acid + ammonium chloride
