+ H* нн cyclopentane н cyclopentyl anion pK, > 60 + H* нн cyclopentadiene н cyclopentadienyl anion pk = 15

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter5: Stereochemistry At Tetrahedral Centers
Section5.5: Sequence Rules For Specifying Configuration
Problem 8P
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The pKa of cyclopentane is > 60, which is about what is expected for a hydrogen that is bonded to an sp3 carbon. Explain why cyclopentadiene is a much stronger acid (pKa of 15) even though it too involves the loss of a proton from an sp3 carbon.

+ H*
нн
cyclopentane
н
cyclopentyl anion
pK, > 60
+ H*
нн
cyclopentadiene
н
cyclopentadienyl
anion
pk = 15
Transcribed Image Text:+ H* нн cyclopentane н cyclopentyl anion pK, > 60 + H* нн cyclopentadiene н cyclopentadienyl anion pk = 15
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