Which of the following compounds can be prepared in good yield by Gabriel phthalimide synthesis?
(A)(see structure)✓ Correct
(B)CH₃-CH₂-NHCH₃
(C)(see structure)
(D)(see structure)
Answer: (A)
Solution
Gabriel's phthalimide synthesis makes primary amines, because it works by the phthalimide anion displacing halide from an alkyl halide in an SN2 step, and aryl halides will not undergo that substitution. Among the choices, benzylamine, CX6HX5CHX2NHX2, is a primary amine whose benzyl halide reacts cleanly, so benzylamine is the one obtained in good yield; the secondary amine, the amide and aniline cannot be made this way.
JEE Main · 2020 · 06 Sep 2020 · Shift 2 · Single correct option
