Basic IUPAC Organic Nomenclature

Nitriles

Nomenclature	Formula	3D structure
Functional class = alkyl cyanide Functional group suffix = nitrile or -onitrile Substituent prefix = cyano- Notes : The cyano prefix is used in a very similar manner to haloalkanes The cyano nomenclature is most common when the alkyl group is simple. The nitrile suffix is used in a very similar manner to carboxylic acids.

• The root name is based on the longest chain with the -C≡N as a substituent.
  
• This root give the alkane part of the name.
  
• The chain is numbered so as to give the -C≡N group the lowest possible locant number

• The root name is based on the longest chain including the carbon of the nitrile group.
• This root give the alkyl part of the name.
• Since the nitrile must be at the end of the chain, it must be C1 and no locant needs to be specified.
  
• Nitriles can also be named by replacing the -oic acid suffix of the corresponding carboxylic acid with -onitrile.
  

Cyano substituent style: Functional group is an alkane, therefore suffix = -ane The longest continuous chain is C3 therefore root = prop The substituent is a -CN therefore prefix = cyano The first point of difference rule requires numbering from the right as drawn, the substituent locant is 1- 1-cyanopropane Nitrile style: Functional group is a -C≡N, therefore suffix = -nitrile Hydrocarbon structure is an alkane therefore -ane The longest continuous chain is C4 therefore root = but butanenitrile

CH3CH2CH2C≡N

© Dr. Ian Hunt, 2005, Department of Chemistry, University of Calgary