production and uses of amines

give 3 ways of producing amines and state which type of amine they can produce:

• reaction of XS NH₃ w/ XS haloalkanes - aliphatic

• reduction of nitriles (C≡N) - aliphatic

• reduction of nitro compounds (NO₂) - aromatic

give the general eqn for the reaction of NH₃ w/ haloalkanes to form a 1^o amine:

(where R = alkyl group and X = halogen)

R-X + 2NH₃ → R-NH₂ + NH₄X

give an issue with using the reaction between NH₃ and XS haloalkanes to make primary amines:

• products undergo further substitution

• this results in a mixture of products (primary, secondary, tertiary and quaternary ammonium salts)

outline the mechanism for the reaction between XS 1-bromopropane and (sufficient) ammonia:

give the final product of a nuc sub reaction w/ NH₃ and XS 2-bromopropane:

give the final product of a nuc sub reaction w/ 2-bromopropane and XS NH₃:

outline the mechanism and eqns for the reaction between bromomethane and potassium nitrile (reduction of nitriles):

which catalyst catalyses the reduction of nitriles?

nickel (Ni)

why is reduction of nitriles the preferred method for making aliphatic 1^o amines?

• only one amine formed

• increases C chain length - useful

describe the process of making aromatic amines:

reduction of nitro compounds:

1. heat nitro compound, tin metal and conc HCl under reflux

2. (add NaOH solution)

give the eqn for the reaction between nitrobenzene and hydrogen (reduction of nitro compounds):

give 2 uses for quaternary ammonium salts:

• cationic surfactants

• fabric softener as many fabrics have a -ve charge on surface

give one use of aromatic amines:

used in the manufacture of dyes