ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS
ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS
6th Edition
ISBN: 9781260325294
Author: SMITH
Publisher: RENT MCG
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Chapter 12.5, Problem 12P
Interpretation Introduction

(a)

Interpretation: The product formed when the given compound is treated with H2 (excess), Pd-C is to be predicted.

Concept introduction: The addition of H2 in presence of catalyst is known as catalytic hydrogenation reaction. This is a syn addition. Alkyne is reduced to alkane. In this reaction, two weak pi bond of alkyne and sigma bond between H2 is broken and four CH bonds are formed.

Interpretation Introduction

(b)

Interpretation: The product formed when the given compound is treated with H2 (1 equiv.), Lindlar catalyst is to be predicted.

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 presence of Lindlar catalyst alkyne is reduced to cis-alkene.

Interpretation Introduction

(c)

Interpretation: The product formed when the given compound is treated with H2 (excess), Lindlar catalyst is to be predicted.

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 presence of Lindlar catalyst alkyne is reduced to cis-alkene.

Interpretation Introduction

(d)

Interpretation: The product formed when the given compound is treated with Na,NH3

is to be predicted.

Concept introduction: In presence of sodium metal in ammonia, the is alkyne is reduced to trans-alkene. The addition of H2 takes place in anti fashion to the triple bond. The mechanism involves the addition of electron followed by protonation.

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Chapter 12 Solutions

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