9. When [Fe(CO)5] is refluxed with cyclopentadiene, compound A is formed, which has the empirical formula C8H6O3Fe, and a complicated 'H nmr spectrum. Compound A readily loses CO to give compound B, which has two 'H nmr resonances, one at negative chemical shift and relative intensity one, and the other at around 5 ppm with relative intensity of five. Subsequent heating of B results in the loss of H₂ and the formation of C. Compound C has a single 'H nmr resonance and the empirical formula C₂H5O₂Fe. Treatment of C with iodine results in D, FeC₂H5O₂I. Treatment of C with potassium metal, followed by CH3Br, yields E. Propose structures for A - E.

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
Section: Chapter Questions
Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...
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9. When [Fe(CO)s] is refluxed with cyclopentadiene, compound A is formed, which has the
empirical formula C8H6O3Fe, and a complicated 'H nmr spectrum. Compound A readily loses
CO to give compound B, which has two 'H nmr resonances, one at negative chemical shift and
relative intensity one, and the other at around 5 ppm with relative intensity of five. Subsequent
heating of B results in the loss of H₂ and the formation of C. Compound C has a single 'H nmr
resonance and the empirical formula C₂H5O₂Fe. Treatment of C with iodine results in D,
FeC₂H5O₂I. Treatment of C with potassium metal, followed by CH3Br, yields E.
Propose structures for A - E.
Transcribed Image Text:9. When [Fe(CO)s] is refluxed with cyclopentadiene, compound A is formed, which has the empirical formula C8H6O3Fe, and a complicated 'H nmr spectrum. Compound A readily loses CO to give compound B, which has two 'H nmr resonances, one at negative chemical shift and relative intensity one, and the other at around 5 ppm with relative intensity of five. Subsequent heating of B results in the loss of H₂ and the formation of C. Compound C has a single 'H nmr resonance and the empirical formula C₂H5O₂Fe. Treatment of C with iodine results in D, FeC₂H5O₂I. Treatment of C with potassium metal, followed by CH3Br, yields E. Propose structures for A - E.
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