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Amines
AQA A-level chemistry amines organic year 13
| Term | Definition |
|---|---|
| Amines | An organic derivative of ammonia (NH3) in which one or more of its hydrogen atoms have been substituted with an alkyl or aryl group |
| Why aliphatic amines are stronger bases than ammonia | Because alkyl groups have an inductive effect of increasing the electron density around the central nitrogen which makes amines more efficient proton acceptors than ammonia |
| Why ammonia is a stronger base than phenylamines | This is because the lone pair in the nitrogen of a phenylamine is delocalised into the benzene ring which make it less accessible for proton acceptance than ammonia |
| How amines and N-substituted amines are created | To create amines an ammonia molecule undergoes nucleophilic substitution with a haloalkane and another ammonia as a weak base, for N-substituted amines there needs to be an excess of haloalkane compared to the ammonia |
| What happens a fourth alkyl group is substituted onto a tertiary amine | A quaternary ammonium salt is formed with the halogen from the haloalkane |
| Cationic surfactants | Surface-active molecules with a positively charged cation in their structure. This makes them both hydrophilic and lipophilic so it can neutralise negative charges, bind to polar molecules, and disperse non-polar molecules |
| How primary aliphatic (alkyl) amines are prepared | With either the reduction of ammonia with haloalkanes or the reduction of nitriles |
| How primary phenyl (aryl) amines are prepared | With the reduction of nitrobenzenes |
| Reduction of ammonia with haloalkanes: formula | RCH2Br + NH3 - RCH2NH3+ + Br- RCH2NH3+ + NH3 + Br- - RCH2NH2 + NH4Br |
| Production and reduction of nitriles: formula | RCH2Br + KC=-N - RCH2C=-N + KBr RCH2C=-N + 4[H] -(LiAlH4)- RCH2CH2NH2 OR RCH2C=-N + 2H2 -(Ni + high temp. & press.)- RCH2CH2NH2 |
| Production and reduction of nitrobenzene: formula | C6H6 + NO2+ -(AlCl4-)- C6H5NO2 + HCl C6H5NO2 + 6HCl -(Sn)- C6H5NH3Cl + 2H2O C6H5NH3Cl + NaOH - C6H5NH2 + H2O + HCl |
| Amphoteric | Contain both acidic and basic groups |
| Amino acid general structure | Contain an amine group, a carboxyl group, a central carbon with a hydrogen, and a variable organic side chain (except for glycine) and are chiral so they can rotate plane polarised light |
| Zwitterions | A molecule which contains both a cation and anion in its structure making it electrically neutral |
| Isoelectric point | The PH at which a molecule carries no net electrical charge due to there being an equal number of protons and deprotonated groups. In amino acids, the isoelectric point is determined by the R group |
| Terylene | Polyester made from benzene dicarboxylic acid and butan-1,4-diol |
| Kevlar | Polyaramide made from benzene di-1,3-carboxylic acid and phenyl-1,3-amine |
| Nylon | Polyamide made from butan-1,4-dioic acid and hexan-1,6-diammine |
| Cisplatin (cis-diamminodichloroplatinum (II)) | Anti cancer drug, especially useful for testicular & ovarian cancer. Replaces chlorine atom with nitrogen from guanine & repeats with the other to fix to the DNA & distort it & prevents replication. Transplantin doesn’t work |
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