Q13 / 54 · JEE Advanced 2022 (Paper 1) · Chemistry

Considering the reaction sequence given below, the correct statement(s) is(are)

Figure

  • A
    P can be reduced to a primary alcohol using NaBH4.
  • Correct answer
    B
    Treating P with conc. NH4OH solution followed by acidification gives Q.
  • Correct answer
    C
    Treating Q with a solution of NaNO2 in  aq.HCl liberates N2.
  • Correct answer
    D
    P is more acidic than CH3CH2COOH.

Solution

Propanoic acid is having  α-hydrogen hence it is halogenated at the α-position on treatment with chlorine or bromine in the presence of small amount of red phosphorus to give α-bromo propanoic acid. The reaction is known as Hell-Volhard-Zelinsky reaction.

Second step of the reaction involves Gabriel phthalimide synthesis Where potassium salt of phthalimide which on heating with 2-bromo propanoic acid  followed by alkaline hydrolysis produces the corresponding 2-amino propanoic acid. Aromatic primary amines cannot be prepared by this method.​​​​​​Figure

NaBH4 cannot reduce the acids.

Conc. NH4OH exist in the following equilibrium,

NH4+  + OH-⇋NH3+H2O

Figure

Hence, the correct answer is options: 'B', 'C', 'D'.

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