An unknown molecule displays 1 H NMR and IR spectra D (next page). Reaction with H 2

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An unknown molecule displays 1H NMR and IR spectra D (next page). Reaction with H2 in the presence of the Lindlar catalyst gives a compound that, after ozonolysis and treatment with Zn in aqueous acid, gives rise to one equivalent of 

00 CH;CCH and two of HCH.

What was the structure of the original molecule?

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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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