47
Question
Why is pyrrole more acidic than pyrrolidine?
Step-by-Step Solution
Verified Answer
Pyrrole is more acidic than pyrrolidine because its conjugate base is more stable than pyrrolidine.
1Resonance
The continuous delocalization of the pi electrons in the conjugative system leads to many contributing structures. This concept is known as resonance.
2Explanation
In the conjugate base of pyrrole, there is delocalization of the electron pair within the ring. Due to this, its basicity decreases. Thus, it has a weaker conjugate base.
But there is no resonance in the conjugate base of pyrrolidine, so it has a stronger conjugate base.
Thus, pyrrole is more acidic than pyrrolidine.
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