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Question

A compound named 5-(-1-Cyanoethyl)-2-methyl hexanoic acid has something wrong according to IUPAC. What is correct IUPAC name? 
  1. 5-Ethylcyanide-2-methylhexanoic acid 
  2. 6-Cyano-2,5-dimethylheptanoic acid 
  3. 6-Cyano-5-methyl-2-heptanoic acid 
  4. 6-Carboxy-2,3-dimethylheptanenitrile


Solution

The correct option is B 6-Cyano-2,5-dimethylheptanoic acid 
As CN is behaving as substituent here because priority order of carboxylic acid is on the top.

Carboxylic acids ( -COOH )
Suffix: oic acid/carboxylic acid

Nitriles ( -C≡N )
Prefix :  cyano
Alkyl(-R) group do not have any priority order and considered  substituents while numbering

The compound with correct numbering of parent chain is 
Hence, correct IUPAC name is 
6-Cyano-2,5-dimethylheptanoic acid 

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