Nitrogen Organic Flashcards
Amine properties (6)
Lp: nucelophile or base
Triangular pyramid
Polar
Hb to each other/water (C<4)
SC, gas, rtp
Fishy smell
Which amine isn’t soluble and why
Phenylamine
Large benzene ring
Energetic profit
Amide properties
C=O and N
Solid rtp (except methanamide)
HB, dimer
Soluble (HB N+O)
Amino acid properties (4)
Protein monomer
COOH + NH2
20 natural occurring
Chiral/optically active
5 types of amino acid R group
Non polar
Polar
Aromatic
+ve charged
-ve charged
Name 2 ways of making amines
Reducing nitriles
Nucleophilic substitution
Amine preparation via nitrile reduction
LiAlH4
Dry ether/dilute HCl
Or
H2
High temp/press
Ni catalyst
Amine production via nucleophilic substitution
Excess, conc ethanolic NH3
Slight pressure
Makes NH4Cl
Amine production via nucleophilic substitution further substitutions
Excess NH3, mostly primary
Excess haloalkane, mixture
Amines themselves are nucleophile/lps
Quaternary use din fabric softener
Pheylamine acid reaction
Basic
—> NaOH + NH3+ benzene
Nitrobenzene reduction
Tin
Conc HCl
Oxidised
Makes H2
NO2 —> NH2
Phenylamine steam distillation
Separate from aq impurities
Org compounds may decompose before bp
cant use simple distillation
Steam lowers bp
Immsicible water + Phenylamine mixture
Acid base amine reactions
Bond to H+/proton acceptor
Dative covalent bond
e- C becomes nucleophile
Higher e- density/lp availability/base strength
Proton accepting/lp donation more likely
Basicity
Ka/pKa
Ability to donate lp to H2O H+
Increase no. Alkyl groups around around N, increase e-s released, increase proton acceptance, increase lp donation to H+
Methylamine basicity
Methyl e-s released to N
+ve inductive effect
Increase N e- density
More delta -ve
easier proton acceptance/H+ lp donation
Ethyl propyl basicity
Increase no e-s —> N
Increase basicity
Phenylamine basicity
N lp e-s —> phenyl group
Lp/delocalised e- overlap in benzene ring
Lp —> delocalised system
Decrease N e- density
Decrease lp donation to H+
Ammonia and amine reactions with water
Reversible
Make positive ammonium/anime ion and OH-
Dissolve
Alkaline solutuon
Amine reactions with acid
React with strong acids —> ionic salts
Amine reaction with Cu2+
Ligand exchange
Transition metals + N dative covalent bond
(Cu(H2O)OH) + NH3 —> (Cu(H2O)NH3) + H2O + OH-
Pale blue ppte —> deep blue solution
Amine acylation
Primary amines/ammonia and Acyl chlorides
Rtp
Misty HCl fumes
Make an amine
Amine and acid react to make amine chloride salt
N sub amine
Paracetamol synthesis
Add/elim
Phenol
HNO3 + H2SO4 (nitro phenol)
Tin + conc HCl (amino phenol)
CH3COCl (amide phenol)
What 3 functional groups does paracetamol have
Amide group
Benzene ring
Hydroxyl group
Amino acid charge and basicity properties
Acidic CA group, loss proton
Basic AG groups, accept proton
Zwitterion
Permanent +ve/-ve
Overall neutral charge
I so electronic
pH = charge 0
