Alkanenitriles A Special Class of Carboxylic Acid Derivatives

ALKANENITRILES A SPECIAL CLASS OF CARBOXYLIC ACID DERIVATIVES 

Nitriles, RC=N, are considered derivatives of carboxylic acids because the nitrile carbon is in the same oxidation state as the carboxy carbon and because nitriles are readily converted into other carboxylic acid derivatives. This section describes the rules for naming nitriles, the structure and bonding in the nitrile group, and some of its spectral characteristics. Then it compares the chemistry of the nitrile group with that of other carboxylic acid derivatives. 

In lUPAC nomenclature nitriles are named from alkanes 

A systematic way of naming this class of compounds is as alkanenitriles. In common names, the ending -ic acid of the carboxylic acid is usually replaced with -nitrile. The chain is numbered like those of carboxylic acids. Similar rules apply to dinitriles daived from dicarboxylic acids. The substituent CN is called cyano. Cyanocycloalkanes are called cyclo-alkanecarbonitriles. We will retain the common name benzonitrile (from benzoic add), rather than use the systanatic benzenecarbonitrile. 

In the nitriles, both atoms in the functional group are sp hybridized and a lone electron pair on nitrogen occupies an sp hybrid orbital pointing away from the molecule along the C-N 

---