JEE MainChemistryHaloalkanes and Haloarenes
1-Bromo-4-chloropentane is reacted with 1 molar equivalent of KCN to form major product P. P is then reacted with 1 molar equivalent of AgNO ₂ to form major product Q. The IUPAC name of Q is:
Options
- A5-nitrohexanenitrile
- B2-methyl-5-nitropentanenitrile
- C5-nitritohexanenitrile
- D1-isocyano-5-nitrohexane
Correct answer
A. 5-nitrohexanenitrile
Step-by-step solution
1-Bromo-4-chloropentane has a primary bromide and a secondary chloride. Bromide is a better leaving group than chloride, and primary halides are more reactive towards S_N2 reactions than secondary halides. Thus, KCN selectively substitutes the bromine atom. Since KCN is predominantly ionic, the ambident cyanide ion attacks through the carbon atom to form a nitrile. Product P is 5-chlorohexanenitrile. Product P is then reacted with AgNO ₂ . The remaining chloride is substituted. Since AgNO ₂ is predominantly covalen