ORG CHEM CONNECT CARD
ORG CHEM CONNECT CARD
6th Edition
ISBN: 9781264860746
Author: SMITH
Publisher: MCG
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Chapter 12.5, Problem 10P
Interpretation Introduction

Interpretation: The structure of cis-jasmone, formed by treatment of alkyne A with H2 in the presence of the Lindlar catalyst is to be drawn.

Concept introduction: The addition of H2 in presence of catalyst is known as catalytic hydrogenation reaction. Lindlar catalyst consists of palladium deposited on calcium carbonate which is poisoned or deactivated by lead or sulfur. In the presence of Lindlar catalyst, alkyne is reduced to cis-alkene.

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What is the structure of cis-jasmone, a natural product isolated from jasmine flowers, formed by treatment of alkyne A with H2 in the presence of the Lindlar catalyst?
What is the structure of cis-jasmone, a natural product isolated from jasmine flowers, formed by treatment of alkyne A with H2 in the presence of the Lindlar catalyst?
a) What is the major alkene formed when A is dehydrated with H2SO4? (b) What is the major alkene formed when A is treated with POCl3 and pyridine? Explain why the major product is different in these reactions.

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