Question

What advantages are there to using piperidine rather than hydroxide as a base?

Answer 1

Advantages of using piperidine rather than hydroxide as a base :

1) As hydroxide is polar in nature and it is not soluble in all the organic solvents but piperidine is miscible in water as well in organic solvents like alcohol, benzene, chloroform .

2) It can also be used as secondary amine in addition to base as it can contain nitrogen group and does not contain any double bonds where lone pair electrons on nitrogen group are not withdrawn i.e. more nucleophilic in nature. But in hydroxides the lone pair electrons on oxygen are withdrawn hence less nucleophilic in nature.

3) The pKa value of piperidine is 11 where as hydroxides has pKa value in the range of 13-15. Hence piperidine remains in the cationic form from the pH values of 5-9 and volatilization from water surfaces do not occur.