addition of hydrogen cyanide to form hydroxynitriles Flashcards
What is formed?
= carboynyl => hydroxynitrile
What is the reagant?
= sodium cyanide
= NaCN + dilute sulfuric acid
What are the conditions?
= room pressure and room temperature
What ions are supplied?
= NaCN: CN^- ions
= H2SO4: supplies a H+ ion (acid)
Why cant we use HCN?
= toxic gas
= difficult to contain
=
What are the advantages of using KCN and NaCN?
= higher concentration of CN- ions
= compiunds will completley ionise
= HCN is a weak acid and will partianlly ionise
What is the mechanism?
= the cyanide nucleophile is attracted to the partially positive electron defficient carbon and forms a covalent bond with the C=O bond,
= carbon can only have 4 covalent bonds so one of the bonds of the double C=O bond breaks with both electrons going to oxygen
= the lone pair of electrons with the oxygen are attracted to the H+ ion from the acid and forms a covalnt bond