18B Organic Nitrogen Flashcards
what is functional group for amines?
R-NH2
what is the functional group for amides?
R-C=ONH2
de-esterification of esters
r - NH3 (aq)
c - reflux
p - amide
nucleophilic addition of acyl chlorides
r - NH3 (aq) or conc. HCl
c - room temp
p - amide
dehydration of carboxylic acids
r - NH3 (aq)
c - reflux
p - amide
hydrolysis of amides
r - HCl (aq) or H2SO4 (aq)
c - reflux
p - carboxylic acid
dehydration of amides
r - P4O10
c - reflux
p - nitrile
hydrolysis of nitriles
r - HCl (aq) or NaOH (aq)
c - reflux
p - amide
hoffman degradation of amides
r - Br2, NaOH (aq)
c - reflux
p - amine
nucleophilic addition of amines
r - acylchloride
c - reflux
p - secondary amide
nucleophilic substitution of halogenoalkanes (Sn) to form amines
r - conc. NH3 in ethanol
c - heat in a sealed tube
p - amine
reduction of nitriles
r - LiAlH4
c - dry ether, reflux
p - amine
neutralisation of amines
r - HCl (aq) or H+ (aq)
c - room temp
p - R-NH3+Cl-
acylation of amines
r - RCOCl
c - room temp
p - secondary amide
amines to amines acting as a base
r - water
c - room temp
p - R-NH3+ OH-
ligand exchange of amines
r - [Cu(H2O)6]2+ (aq)
c - room temp
p - copper complex ion
[Cu-R-H20]2+
secondary, tertiary amine formation from primary amine
r - excess CH3CH2Cl in ethanol
c - reflux
p - amine
nucleophilic substitution of halogenoalkanes (Sn) to form nitriles
r - KCN, ethanol
c - reflux
p - nitrile
hydrolysis of nitriles
r - HCl (aq)
c - reflux
p - amides
how are hydroxynitriles formed from carbonyls?
r - KCN, H2SO4
c - reflux, pH 8 buffer
p - hydroxynitrile
hydrolysis of dipeptides
r - conc. HCl (aq) , H2O
c - reflux
p - amino acid
describe amphoteric behaviour
when something acts as both an acid and a base
how are polyamides formed?
from the reaction between dicarboxylic acids and diamines
elimination of water results in long chain polymers
monomer units are linked with amide bonds
what else can be used to make polyamides?
diacylchlorides
HCl is lost instead of water so should be done in fume cupboard
define the term base
proton acceptor / lone pair donator
what makes an organic compound more basic?
more alkyl groups inductively donating and stabilising the resulting ion
why is ethanamide a weak base compared to an aliphatic primary amine?
delocalised lone pair creates resonance structure with C=O so it becomes less available for bonding
what colour do amino acids turn in ninhydrin?
purple/pink/red
explain why excess ammonia is needed in organic synthesis
product acts as nucleophile
further substitution occurs
excess NH3 reduces chance of further subsititution
state the feature of an amine that allows it to act as a Bronsted-Lowry base
lone pair of e- on N
why are aliphatic amines stronger bases?
alkyl groups that can push e- (inductive effect)
makes lone pairs more available
why is ammonia a stronger base than phenylamine?
lone pair on N delocalises
less available for bonding
what is meant by the term zwitterion
neutral molecule
has +NH3 and COO- groups
formed through proton transfer
