Formation of Nitriles
Carbon-carbon bond forming
- Carbon–carbon bond forming reactions are organic reactions in which a new carbon–carbon bond is formed
- They are important in the production of many man-made chemicals such as pharmaceuticals and plastics
- Carbon-carbon bonds can be formed via the following reactions
- Formation of nitriles to extend the carbon chain
- Frieidel-Crafts alkylation and acylation
Formation of nitriles
- The nucleophile in this reaction is the cyanide, CN- ion
- Ethanolic solution of potassium cyanide (KCN in ethanol) is heated under reflux with the halogenoalkane
- The product is a nitrile
- Eg. bromoethane reacts with ethanolic potassium cyanide when heated under reflux to form propanenitrile
The halogen is replaced by a cyanide group, CN -
- The nucleophilic substitution of halogenoalkanes with KCN adds an extra carbon atom to the carbon chain
- This reaction can therefore be used by chemists to make a compound with one more carbon atom than the best available organic starting material
Nucleophilic substitution of a haloalkane with CN-
Addition of HCN to carbonyl compounds
- The nucleophilic addition of hydrogen cyanide to carbonyl compounds is a two-step process, as shown below
- In step 1, the cyanide ion attacks the carbonyl carbon to form a negatively charged intermediate
- In step 2, the negatively charged oxygen atom in the reactive intermediate quickly reacts with aqueous H+ (either from HCN, water or dilute acid) to form 2-hydroxynitrile compounds,
- e.g. 2-hydroxypropanenitrile