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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

  1. A5-nitrohexanenitrile
  2. B2-methyl-5-nitropentanenitrile
  3. C5-nitritohexanenitrile
  4. 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

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