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JEE Advanced · Chemistry · 27. Carboxylic Acids

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

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

Answer & Solution

Correct Answer

(B) Treating P with conc. NH4OH solution followed by acidification gives Q.

Step-by-step Solution

Detailed explanation

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.​​​​​​

NaBH4 cannot reduce the acids.
Conc. NH4OH exist in the following equilibrium,
NH4+  + OH-NH3+H2O
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