JEE Main · 2004 · 24 Apr 2004 · Offline · Compounds Containing Nitrogen

Which of the following is the strongest base?

(A)(see structure)
(B)(see structure)
✓ Correct
(C)(see structure)
(D)(see structure)

Answer: (B)

Solution

Base strength here depends on how freely the nitrogen lone pair is offered to a proton. In benzylamine,

C X_{6} H X_{5} CH X_{2} NH X_{2}

, the

NH X_{2}

hangs off an

s p^{3}

CH X_{2}

that insulates it from the ring, so the lone pair stays localised and fully basic. In aniline and in N-methylaniline the lone pair is drawn into the aromatic ring and so is less available, while the ortho-substituted amine suffers steric crowding. Benzylamine therefore stands out as the strongest base.

JEE Main · 2004 · 24 Apr 2004 · Offline · Single correct option

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