In the reaction shown below, the major product(s) formed is/are
(A)(see structure)✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)
Answer: (A)
Solution
The reaction involves a Gabriel phthalimide synthesis followed by hydrolysis. The starting material is N-substituted phthalimide. Treatment with aqueous base (NaOH) followed by acidification hydrolyzes the imide, cleaving both C-N bonds to release the primary amine and phthalic acid. The major product is the primary amine shown in option (A). The mechanism involves nucleophilic attack by hydroxide on the carbonyl carbons, opening the imide ring and releasing the amine. Option (A) is the correct product.
JEE Advanced · 2014 · 25 May 2014 · Paper 1 · One or more correct options
