All the molecules shown below are examples of fulvenes, or methylenecyclopentadienes. (a) One of these structures is

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All the molecules shown below are examples of “fulvenes,” or methylenecyclopentadienes.

N(CH3)2 H3C CH3 C,H5. C,Hs 5-Methylene- 1,3-cyclopentadiene

(a) 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.

(b) None of the 7-methylene-1,3,5-cycloheptatrienes that correspond to the fulvene structures above show any unusual acidity. Explain.

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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Question Posted: May 06, 2020 03:38 AM

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All the molecules shown below are examples of fulvenes, or methylenecyclopentadienes. (a) One of these structures is

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N(CH3)2 H3C CH3 C,H5. C,Hs 5-Methylene- 1,3-cyclopentadiene "Fulvene" 6-Dimethylamino- 6,6-Dimethyl- fulvene 6,6-Diphenyl- fulvene fulvene

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Organic Chemistry structure and function

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