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Basics of Organic Chemistry question

2024 · 9 Apr · Shift 1 · Q12
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Basics of Organic Chemistry question

2024 · 9 Apr · Shift 1 · Q12

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Correct order of basic strength of Pyrrole JEE Main 2024 (Online) 9th April Morning Shift Chemistry - Basics of Organic Chemistry Question 59 English 1, Pyridine JEE Main 2024 (Online) 9th April Morning Shift Chemistry - Basics of Organic Chemistry Question 59 English 2 and Piperidine JEE Main 2024 (Online) 9th April Morning Shift Chemistry - Basics of Organic Chemistry Question 59 English 3 is :
  1. A
    Pyridine > Piperidine > Pyrrole
  2. B
    Pyrrole > Piperidine > Pyridine
  3. C
    Pyrrole > Pyridine > Piperidine
  4. D
    Piperidine > Pyridine > Pyrrole
View written solutionFree

Correct answer: D

  1. Basicity depends on availability of the lone pair on nitrogen for donation to a proton.

  2. Piperidine:

    • Piperidine is a saturated aliphatic amine.
    • The lone pair on nitrogen is localized and easily available for protonation.
    • Hence, it is strongly basic.
  3. Pyridine:

    • In pyridine, nitrogen is sp2sp^2sp2 hybridized.
    • Its lone pair lies in an sp2sp^2sp2 orbital and is not involved in the aromatic sextet.
    • So it is available for protonation, but due to greater sss-character of sp2sp^2sp2 orbital, it is held more tightly than in piperidine.
    • Therefore, pyridine is less basic than piperidine.
  4. Pyrrole:

    • In pyrrole, the lone pair on nitrogen is part of the aromatic sextet.
    • If this lone pair is donated to a proton, aromaticity is lost.
    • Therefore, the lone pair is least available for protonation.
    • Hence, pyrrole is very weakly basic.
  5. Therefore, the correct order of basic strength is Piperidine>Pyridine>Pyrrole\text{Piperidine} > \text{Pyridine} > \text{Pyrrole}Piperidine>Pyridine>Pyrrole

  6. Checking options:

    • A: Pyridine>Piperidine>Pyrrole\text{Pyridine} > \text{Piperidine} > \text{Pyrrole}Pyridine>Piperidine>Pyrrole ❌
    • B: Pyrrole>Piperidine>Pyridine\text{Pyrrole} > \text{Piperidine} > \text{Pyridine}Pyrrole>Piperidine>Pyridine ❌
    • C: Pyrrole>Pyridine>Piperidine\text{Pyrrole} > \text{Pyridine} > \text{Piperidine}Pyrrole>Pyridine>Piperidine ❌
    • D: Piperidine>Pyridine>Pyrrole\text{Piperidine} > \text{Pyridine} > \text{Pyrrole}Piperidine>Pyridine>Pyrrole ✅

So, the correct answer is D.

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