Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 14, Problem 14.45AP
Interpretation Introduction

Interpretation:

The structure of compound A is to be proposed with the help of given information.

Concept introduction:

Ozonolysis is the oxidative cleavage of the double bond, where C=C bond breaks and the formation of C=O bond takes place. During oxidative cleavage, the formation of ketone or aldehyde takes place. Lindlar catalyst contains palladium which is deposited on calcium carbonate. Lindlar catalyst is used for hydrogenation of alkynes or alkenes.

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An unknown hydrocarbon A with the formula C6H10 reacts with 1 molar equivalent of H2 over a palladium catalyst to give B C6H12 (Rxn 1). Hydrocarbon A also reacts with OsO4 to give the glycol C (Rxn 2). A gives 5-oxohexanal on ozonolysis (Rxn 3).  Draw the structures of A, B, and C. Give the reactions.
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