Presentation on theme: "Amines as nucleophiles and their synthesis"— Presentation transcript:
1Amines as nucleophiles and their synthesis L.O.:Understand the reaction of amines and ammonia with haloalkanes.Know one application of quaternary ammonium salts.Know how amines can be prepared from nitriles.Know how aromatic amines can be prepared from nitro compounds.
2Consider the reaction between ethylamine and an excess of bromoethane Write the mechanism for the nucleophilic reaction.Consider what type of product you got. Would it react with an excess of bromoethane?Write down all the possible products you may get in the reaction.
3NUCLEOPHILIC SUBSTITUTION PPT - AminesNUCLEOPHILIC SUBSTITUTION25/03/2017Lone pair on N can attack + C of haloalkane.XCHNH2C+X-NH3NH3NH2C-NH4+X
4NUCLEOPHILIC SUBSTITUTION PPT - Amines25/03/2017H on N is swapped by R from haloalkane.Product also has lone pair on N so product reacts further.To get mainly 1y amine use XS NH3.To get mainly 4y ammonium salt use XS RX.
5TASKGive all the organic products formed when methylamine reacts with chloroethane.2) Draw the mechanism for the formation of the tertiary amine in this reaction.3) Draw all the organic products formed when diethylamine reacts with 2-bromopropane
8NUCLEOPHILIC SUBSTITUTION PPT - Amines25/03/20174y ammonium saltsOnes with some long chain alkyl groups can be used as cationic surfactants.Often used in fabric softener as many fabrics have –ve charge on surface.e.g. (CH3)2N[(CH2)16CH3]2+ Cl-
9MAKING ALIPHATIC 1y AMINES PPT - Amines25/03/20171 – Reaction of NH3 with haloalkanesNeed to separate mixture of products.2 – Reduction of nitrile compounds
10Give two synthetic paths to making butylamine Give two synthetic paths to making butylamine. Give equations for all reactions.