Compound A (C9H12) absorbed 3 equivalents of H2 on catalytic reduction over a palladium catalyst to give B (C9H18). On ozonolysis, compound A produced 3 products, C, D and E which was a ketone identified as cyclohexanone. On treatment with NaNH2 in NH3, followed by addition of iodomethane, compound A gave new hydrocarbon, F (C10H14). Draw structures of A, B, C, D and F.

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
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.38P: A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted...
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Compound A (C9H12) absorbed 3 equivalents of H2 on catalytic reduction over a
palladium catalyst to give B (C9H18). On ozonolysis, compound A produced 3 products, C, D
and E which was a ketone identified as cyclohexanone. On treatment with NaNH2 in NH3,
followed by addition of iodomethane, compound A gave new hydrocarbon, F (C10H14). Draw
structures of A, B, C, D and F.

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