5-Methylene- 1,3-cyclopentadiene "Fulvene" 6-Dimethylamino- fulvene 6,6-Dimethyl- fulvene 6,6-Diphenyl fulvene f these structures is considerably more acidic than the others, with a pKa around 20. Identify it and its cidic hydrogen(s), and explain why it is an unusually strong acid for a molecule with only carbon-hydrogen Draw relevant resonance structures to support your answer
5-Methylene- 1,3-cyclopentadiene "Fulvene" 6-Dimethylamino- fulvene 6,6-Dimethyl- fulvene 6,6-Diphenyl fulvene f these structures is considerably more acidic than the others, with a pKa around 20. Identify it and its cidic hydrogen(s), and explain why it is an unusually strong acid for a molecule with only carbon-hydrogen Draw relevant resonance structures to support your answer
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.63P
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Question
![1) All the molecules shown below are examples of "fulvenes."
N(CH3)2
H3C.
CH3
C6H5
C;H5
5-Methylene-
1,3-cyclopentadiene
"Fulvene"
6,6-Dimethyl-
fulvene
6-Dimethylamino-
6,6-Diphenyl
fulvene
fulvene
One of these structures is considerably more acidic than the others, with a pka around 20. Identify it and its
most acidic hydrogen(s), and explain why it is an unusually strong acid for a molecule with only carbon-hydrogen
bonds. Draw relevant resonance structures to support your answer](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fae2e9698-eedc-452f-9edf-a675c5036c1e%2Ff94345a1-33a4-47ae-ba51-10a730368dc3%2F493lvi1_processed.jpeg&w=3840&q=75)
Transcribed Image Text:1) All the molecules shown below are examples of "fulvenes."
N(CH3)2
H3C.
CH3
C6H5
C;H5
5-Methylene-
1,3-cyclopentadiene
"Fulvene"
6,6-Dimethyl-
fulvene
6-Dimethylamino-
6,6-Diphenyl
fulvene
fulvene
One of these structures is considerably more acidic than the others, with a pka around 20. Identify it and its
most acidic hydrogen(s), and explain why it is an unusually strong acid for a molecule with only carbon-hydrogen
bonds. Draw relevant resonance structures to support your answer
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