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
Chapter21: Benzene And The Concept Of Aromaticity
Section21.4: Phenols
Problem 21.6P: Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.
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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
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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