topic 18b: nitrogen chem Flashcards
amINE functional group
r-nh2
to name an amine
alakyl amine
alkan-1-amine
IF SECONDARY eg N methyl propyl amine
amide
n- c= o
amines smell
fishy
amines as bases
- proton acceptors
- lone pair on N can DATIVE COVALEN TBOND with H+
why would a long amine be a better base than ammonia
- more alkyl groups
- +ve inductive effect
- increases e- density on N
phenyl amine as a base?
BAD
lnoe pair on N dissocaties into ring, overlaps with delocalised electron pi structure
amine + acid
- ammonium salt
ionic compound so readily soluble
amine + haloalkane and continue
- nucleophilic substiuttion
to form secondary amine
then tertiary amine
then quaternary ammonium salt
primary amine + acyl chloride
secondary AMIDE
making amine: haloalkane + ammonia
- EETHANOLIC ammonia
forms amine - bad as nu sub continues cos amine produced is also a nu
mixture of products
have to separate
making amine: nitrile
lialh4 in dry ether
DISADAVTANGES vs other methods
1. more steps, more transfer loses, lower yield
KCN is toxic
nitro group
NO2
how to convert a nitro arene to an aryl amine
- tin and hcl
- separate using steam distillation
- forms chloride salt. add naoh to deprotonate
primary amine + acyl chlroide
secondary amide
amino acid alwasy has
amine group
carboxylic acid group
naming amino acid
x amino …anoic acid
carboxylic acid group takes priority
amino acids acc exist as
ZWITTERIONS
ZWITTERION structure
amine part becoms nh3+
carboxylic acid group becomes coo-
high mp of amino acids due to
esa between oppositely charged ions in the zwitterions
in an amino acid, which parts has which bronsted lowry properties
amine group = basic
carboxylic group = acidic
zwitterion in very alkaline
nh2 coo-
zwitterion in very acidic
nh3+ cooh
2 methods of reducing to make an amine
- nitro . tin, hcl, chloride salt so need alkali
- nitrile. lialh4 in dry ether
alternative redcution of nitrile
h2 and nickel catalyst
equation acid + zwitter
h+ + nh3+ch2coo- = nh3+ch2cooh
equation alkali + zwitter
oh- + nh3+ch2coo- = nh2ch2coo- + h2o
how to minimise further substitution
excess of reagent
reaction w lialh4 represented with
+ 4[H]
name CH3C=ONHCH3
methyl ethan amide
