ABC26OR0032 · General Organic Chemistry

Subject: Organic Chemistry · Chapter: General Organic Chemistry · Topic: Acidity Basicity · Exam: CSIR-NET DEC 2014 · Marks: 2 · Difficulty: Hard

The decreasing order of basicity of the following compounds is structure structure structure structure (I) (II) (III) (IV)
(a)I $>$ II $>$ III $>$ IV
(b)IV $>$ I $>$ II $>$ III
(c)III > II > I > IV
(d)IV $>$ III $>$ II $>$ I
Answer
Answer (as printed): C
Explanation
Imidazole is more basic than pyridine. The conjugate acid of imidazole is more stable than conjugate acid of pyridine. The conjugate acid of pyridine eliminates the aromaticity in pyridine. $sp^3$ hybridized nitrogen is more basic than $sp^2$ hybridized nitrogen. Hence (II) and (III) will be more basic than I and IV.

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