Organic nitrogen compounds: Amines, Amides, A.A, proteins

Cindy Lam
Mind Map by Cindy Lam, updated more than 1 year ago
Cindy Lam
Created by Cindy Lam almost 7 years ago
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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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Organic nitrogen compounds: Amines, Amides, A.A, proteins
1 Preparation of Amines
1.1 Ammonia heated under pressure with halogenoalkane
1.1.1 1-3 H substituted by an aryl or alkyl group
1.2 Reduction of aromatic nitro-compounds to form aryl amines *
1.2.1 Reduction of Nitrobenzene using tin and HCl under reflux: -NO2 → NH2
1.2.1.1 Cool, +NaOH → redissolve tin(IV) hydroxide
1.2.1.1.1 Steam distillation
1.2.1.1.1.1 Separate phenylamine and water
1.2.1.1.1.2 Salting out
1.2.1.1.1.2.1 Solvent extraction
1.2.1.1.1.2.1.1 Drying agent: Potassium hydroxide
1.2.1.1.1.2.1.1.1 Final distillation
2 Properties
2.1 Aryl amines
2.1.1 Less volatile, usually liquid
2.1.2 Dissolve in organic solvents, only slightly in water
2.2 Alkyl amines
2.2.1 H-bond → higher m.p
2.2.2 Lower members are gases or volatile liquids
2.3 Strong Bases: lone pair on N
2.3.1 e- shift from alkyl group → primary alkyl amines better that ammonia
2.3.2 aryl amine: e- on N interact with delocalised pi e- → weaker base than NH3
3 Reactions
3.1 NS: With Halogenoalkanes → substituted ammine
3.2 A-E: With AC → N substituted amides
3.2.1 Condensation polymers: polyamides
3.3 Amines form complex ions in similar way to NH3
3.4 ES of phenylamine → 4-aminobenzenesulfonamide
3.4.1 Sulfonamides destroy bacteria
4 Amino Acids
4.1 Contain NH2 and COOH and R group
4.2 Acidic and basic properties
4.2.1 In alkaline soln: acid
4.2.2 In acidic son: base
4.2.3 In neutral soln: zwitterion formed
4.2.3.1 aa can exist as zwitterions in solid state → high mp, dissolve in water. Don't dissolve in organic solvent
4.3 20
4.4 Peptide bond C-N in condensation reaction
4.5 Proteins made up of particular sequence of aa
4.5.1 Can determine structure of protein, e.g. Insulin by Frederick Sanger
4.5.2 Difficult for chemists to synthesise proteins
4.5.2.1 Longer chain = more difficult
4.6 Hydrolysis of proteins
4.6.1 Reflux with d.HCl
4.6.1.1 aa neutralised
4.6.1.1.1 aa separated by paper chromatography
4.6.1.1.1.1 Invisible, so spray with ninhydrin in fume cupboard and dry → purple spots
4.6.1.1.1.1.1 Rf value to identify aa
4.6.1.1.1.2 Sometimes electrophoresis is used
4.7 Optical activity
4.7.1 Most aa form optical isomers
4.7.2 aa in living organisms are L enentiomers
4.7.3 Laboratory synthesis of aa tends to produce racemic mixture of L and D enantiomers
5 Ecstasy (an amine) causes release of serotonin and dopamine in the brain
6 Paracetamol
6.1 Phenol is nitrated using H2SO4 and Sodium nitrate
6.1.1 2-nitrophenol and 4-nitrophenol
6.1.2 Fractional distillation
6.1.2.1 4-nitrophenol is reduced → 4-aminophenol
6.1.2.1.1 Using Sodium tetrahydridoborate(III) in alkaline soln
6.1.2.1.2 + ethanoic anhydride →paracetamol
6.1.2.2 4-nitrophenol ↑bp
6.2 No chiral centres → simpler
7 Azodyes
7.1 Phenylamine + nitrous acid (made in situ) +HCl
7.1.1 <5 degrees
7.1.2 benzenediazonium chloride + water
7.1.2.1 Diazonium compound reactions
7.1.2.1.1 NS: N evolved
7.1.2.1.2 Is strong electrophile
7.1.2.1.2.1 Coupling → strong coloured compounds, no N produced
7.1.2.1.2.1.1 Diazo-compounds are extremely stable and unreactive
7.1.2.1.2.1.2 Extensive delocalised e- system → bright colours
7.1.2.1.2.1.2.1 Dye
8 Polymers
8.1 Nylon
8.1.1 Wallace Hume Carothers
8.1.2 Made from 2 monomers
8.1.2.1 Hexanedioic acid + 1,6-diaminohexane → nylon-6,6
8.1.2.2 Obtained via phenol or cyclohexane
8.1.3 Uses: tights, carpets, ropes
8.2 Kevlar
8.2.1 1st used in 1970s as a replacement for steel in racing car tyres
8.2.2 Resists high temp, low thermal conductivity, high tensile strength, flame, chemical and cut resistant
8.2.3 Uses: cables, tyres, bullet proof vests, ropes, adhesives
8.3 Addition polymerisation
8.3.1 2-propanamide → Poly(propanamide)
8.3.1.1 Crossed linked → gel which absorbs water → soft contact lenses
8.3.1.2 Non-cross-linked → thickener and filler in facial surgery
8.3.2 Ester exchange: Poly(ethylethanoate) + methanol → poly(ethanol) + methylethanoate
8.3.2.1 Solubility varies
8.3.2.2 uses: disposable laundry bags (bags dissolve in wash cycle), viscoelastic gel
8.3.3 Properties of polyamides
8.3.3.1 Links vulnerable to attack under acidic or alkaline conditions
8.3.3.2 Addition polymers of just C and H are difficult to break down → pollution
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