JEE Main Chemistry question

Arrange the following compounds in increasing order of basic strength (aqueous medium): piperidine (I), pyridine (II), piperazine (III), 2,5-dihydro-1-pyrrole (IV).

(A)Correct
(B)
(C)
(D)

Answer: (A)

Solution

Pyridine's nitrogen lone pair sits in an orbital within an aromatic ring and is clearly the weakest base of the four (conjugate acid ), so is placed lowest. Piperazine, a six-membered ring bearing a SECOND nitrogen, is weakened relative to a simple cyclic secondary amine because that

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Question ID VK-150391