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38542
Organic nitrogen compounds: Amines, Amides, A.A, proteins
Description
Chemistry (Organic Chem) Mind Map on Organic nitrogen compounds: Amines, Amides, A.A, proteins, created by Cindy Lam on 04/04/2013.
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chemistry
organic chem
chemistry
organic chem
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Cindy Lam
, updated more than 1 year ago
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Cindy Lam
over 11 years ago
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Resource summary
Organic nitrogen compounds: Amines, Amides, A.A, proteins
Preparation of Amines
Ammonia heated under pressure with halogenoalkane
1-3 H substituted by an aryl or alkyl group
Reduction of aromatic nitro-compounds to form aryl amines *
Reduction of Nitrobenzene using tin and HCl under reflux: -NO2 → NH2
Cool, +NaOH → redissolve tin(IV) hydroxide
Steam distillation
Separate phenylamine and water
Salting out
Solvent extraction
Drying agent: Potassium hydroxide
Final distillation
Properties
Aryl amines
Less volatile, usually liquid
Dissolve in organic solvents, only slightly in water
Alkyl amines
H-bond → higher m.p
Lower members are gases or volatile liquids
Strong Bases: lone pair on N
e- shift from alkyl group → primary alkyl amines better that ammonia
aryl amine: e- on N interact with delocalised pi e- → weaker base than NH3
Reactions
NS: With Halogenoalkanes → substituted ammine
A-E: With AC → N substituted amides
Condensation polymers: polyamides
Amines form complex ions in similar way to NH3
ES of phenylamine → 4-aminobenzenesulfonamide
Sulfonamides destroy bacteria
Amino Acids
Contain NH2 and COOH and R group
Acidic and basic properties
In alkaline soln: acid
In acidic son: base
In neutral soln: zwitterion formed
aa can exist as zwitterions in solid state → high mp, dissolve in water. Don't dissolve in organic solvent
20
Peptide bond C-N in condensation reaction
Proteins made up of particular sequence of aa
Can determine structure of protein, e.g. Insulin by Frederick Sanger
Difficult for chemists to synthesise proteins
Longer chain = more difficult
Hydrolysis of proteins
Reflux with d.HCl
aa neutralised
aa separated by paper chromatography
Invisible, so spray with ninhydrin in fume cupboard and dry → purple spots
Rf value to identify aa
Sometimes electrophoresis is used
Optical activity
Most aa form optical isomers
aa in living organisms are L enentiomers
Laboratory synthesis of aa tends to produce racemic mixture of L and D enantiomers
Ecstasy (an amine) causes release of serotonin and dopamine in the brain
Paracetamol
Phenol is nitrated using H2SO4 and Sodium nitrate
2-nitrophenol and 4-nitrophenol
Fractional distillation
4-nitrophenol is reduced → 4-aminophenol
Using Sodium tetrahydridoborate(III) in alkaline soln
+ ethanoic anhydride →paracetamol
4-nitrophenol ↑bp
No chiral centres → simpler
Azodyes
Phenylamine + nitrous acid (made in situ) +HCl
<5 degrees
benzenediazonium chloride + water
Diazonium compound reactions
NS: N evolved
Is strong electrophile
Coupling → strong coloured compounds, no N produced
Diazo-compounds are extremely stable and unreactive
Extensive delocalised e- system → bright colours
Dye
Polymers
Nylon
Wallace Hume Carothers
Made from 2 monomers
Hexanedioic acid + 1,6-diaminohexane → nylon-6,6
Obtained via phenol or cyclohexane
Uses: tights, carpets, ropes
Kevlar
1st used in 1970s as a replacement for steel in racing car tyres
Resists high temp, low thermal conductivity, high tensile strength, flame, chemical and cut resistant
Uses: cables, tyres, bullet proof vests, ropes, adhesives
Addition polymerisation
2-propanamide → Poly(propanamide)
Crossed linked → gel which absorbs water → soft contact lenses
Non-cross-linked → thickener and filler in facial surgery
Ester exchange: Poly(ethylethanoate) + methanol → poly(ethanol) + methylethanoate
Solubility varies
uses: disposable laundry bags (bags dissolve in wash cycle), viscoelastic gel
Properties of polyamides
Links vulnerable to attack under acidic or alkaline conditions
Addition polymers of just C and H are difficult to break down → pollution
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