Reaction of amines with halogenoalkanes 0.0 / 5 ? ChemistryAmines, Amides and amino acidsA2/A-levelEdexcel Created by: Zammi10Created on: 04-03-18 17:46 Why do halogenoalkanes react with amines? Because the halogenoalkane contains an electron-deficient carbon atom and the amine contains an electron rich nitrogen atom 1 of 11 What is this reaction an example of? A substitution reaction 2 of 11 Eg. butylamine+ chloroethane? Gives CH3CH2CH2CH2NHCH2CH3 + HCl 3 of 11 What else occurs? The organic product also contains an electron-rich nitrogen atom so it can also react with chloroethane 4 of 11 What's the new reaction CH3CH2CH2CH2NHCH2CH3 + CH3CH2Cl --> CH3CH2CH2CH2N(CH2CH3)2 + HCl 5 of 11 What is the product? A tertiary amine which again contains a lone pair of electrons so can react with the halogenoalkanes 6 of 11 What is the product this time? CH3CH2CH2CH2N+(CH2CH3)3 + Cl- 7 of 11 Why is HCl not formed this time? Formation of HCl requires the loss of H from the nitrogen of the organic reactant- a tertiary amine does not have a hydrogen attached 8 of 11 What is the salt referred to as? A quaternary ammonium salt 9 of 11 What happens if free secondary and tertiary amines are required? A strong base is added to the solution and the amines formed are extracted from the reaction mixture and separated by fractional distillation 10 of 11 i.e. (C2H5)2NH2+Cl- + OH- --> (C2H5)2NH + H2O + Cl- 11 of 11
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