Question
Considering the reaction sequence given below, the correct statement(s) is(are)
JEE Advanced
Chemistry
Carboxylic Acid Derivatives
2022
JEE Advanced 2022 (Paper 1)
JEE Advanced Chemistry Question (2022) — Solution
Options
- A. P can be reduced to a primary alcohol using NaBH 4 .
- B. Treating P with conc. NH 4 OH solution followed by acidification gives Q .
- C. Treating Q with a solution of NaNO 2 in aq . HCl liberates N 2 .
- D. P is more acidic than CH 3 CH 2 COOH .
Answer
D. P is more acidic than CH 3 CH 2 COOH .
Step-by-step 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. NaBH 4 cannot reduce the acids. Conc .   NH 4 OH exist in the following equilibrium, NH 4 +     +   OH - ⇋ NH 3 + H 2 O
Related: Chemistry — Carboxylic Acid Derivatives · All PYQ Banks