Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 14, Problem 14.46AP
Interpretation Introduction

Interpretation:

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

Concept introduction:

Ozonolysis is the oxidative cleavage of the double bond, where C=C bond breaks and hence the formation of C=O bond takes place. During oxidative cleavage, the formation of ketone or aldehyde takes place. Catalytic hydrogenation is a reaction in which hydrogen atom is added to double or triple bonds in the presence of a catalyst. The catalyst used in these reactions is nickel, palladium and many more.

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An optically active alkyne A (C10H14) can be catalytically hydrogenated to butylcyclohexane. Treatment of A with EtMgBr liberates no gas. Catalytic hydrogenation of A over Pd/C in the presence of quinoline poison and treatment of the product with O3 and then H2O2 gives an optically active tricarboxylic acid C8H12O6 (A tricarboxylic acids is a compound with three - CO2H groups.). Give the structure of A, and account for all observations.
4. Compound A has the formula C 8H 8.  It reacts rapidly with KMnO 4 to give CO 2 and a carboxylic acid, B (C 7H 6O 2), but reacts with only 1 molar equivalent of H 2 on catalytic hydrogenation over a palladium catalyst.  On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H 2 are taken up and hydrocarbon C (C 8H 16) is produced.  What are the structures of A, B, and C.
Nitromethane is reacted with ethyl prop-2-enoate with EtO-Na+, EtOH 3 equivalents to give the product X(C16). X then reacts with H2/Raney Ni to give the product Y(C14), which in turn reacts with Na to give Z (C12). Indicate which products X, Y and Z are.
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