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Chapter 25: 47 (page 1042)

Why is pyrrole more acidic than pyrrolidine?

Short Answer

Expert verified

Pyrrole is more acidic than pyrrolidine because its conjugate base is more stable than pyrrolidine.

Step by step solution

01

Resonance

The continuous delocalization of the pi electrons in the conjugative system leads to many contributing structures. This concept is known as resonance.

02

Explanation

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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Most popular questions from this chapter

Question: Which compound is the stronger base?

Question: What starting materials are needed to synthesize each azo compound?

a.

b.

Question: Rank the following compounds in order of increasing basicity and explain the order you chose.

What amide(s) can be used to prepare each amine by reduction?

(a)

(b)

(c)

Question: What alkyl halide is needed to prepare each 1° amine by a Gabriel synthesis?

a.

b.

c.

See all solutions

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