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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: Draw鈥倀he鈥俻roduct鈥俧ormed鈥倃hen鈥俥ach鈥俢ompound鈥俰s鈥倀reated鈥倃ith鈥侼aNO2鈥俛苍诲鈥侣颁濒.

a.

b.

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d.

Question: Which nitrogen atom in each compound is more basic?

a.

b.

Question: Draw the major product formed in each reaction.

a.

b.

c.

d.

The pKa of the conjugate acid of guanidine is 13.6, making it one of the strongest neutral organic bases. Offer an explanation.

Alkyl diazonium salts decompose to form carbocations, which go on to form products of substitution, elimination, and (sometimes) rearrangement. Keeping this in mind, draw a stepwise mechanism that forms all of the following products.
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