Hydroxynitriles
Contain both a hydroxyl group and nitrile group.
The reaction isn't normally done using hydrogen cyanide itself, because this is an extremely
poisonous gas. Instead, the aldehyde or ketone is mixed with a solution of sodium or potassium
cyanide in water to which a little sulphuric acid has been added.
The nitrile group is the most important as the suffix is nitrile. Hydroxyl is at the beginning of the
name.
Example of a name: (2-hydroxyl-3-methylbutanenitrile)
By convention the formulae for CN- is CN- but in actuality the - charge is on the C.
Addition of hydrogen cyanide to carbonyls to form hydroxynitriles (Nucleophilic
Addition)
Produced by reacting aldehydes, ketones with KCN and then adding a dilute sulphuric acid.
Conditions are: at room temperature and pressure with sodium cyanide and dilute sulphuric
acid.
NaCN supplies the nucleophilic CN- ions. The H2SO4 supplies the H+ ions needed in the
second step.
1. The CN- ion is attracted to the positively charged carbon. It donates a pair of electrons
forming a bond with the carbon.
Contain both a hydroxyl group and nitrile group.
The reaction isn't normally done using hydrogen cyanide itself, because this is an extremely
poisonous gas. Instead, the aldehyde or ketone is mixed with a solution of sodium or potassium
cyanide in water to which a little sulphuric acid has been added.
The nitrile group is the most important as the suffix is nitrile. Hydroxyl is at the beginning of the
name.
Example of a name: (2-hydroxyl-3-methylbutanenitrile)
By convention the formulae for CN- is CN- but in actuality the - charge is on the C.
Addition of hydrogen cyanide to carbonyls to form hydroxynitriles (Nucleophilic
Addition)
Produced by reacting aldehydes, ketones with KCN and then adding a dilute sulphuric acid.
Conditions are: at room temperature and pressure with sodium cyanide and dilute sulphuric
acid.
NaCN supplies the nucleophilic CN- ions. The H2SO4 supplies the H+ ions needed in the
second step.
1. The CN- ion is attracted to the positively charged carbon. It donates a pair of electrons
forming a bond with the carbon.
