Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
Author: KARTY, Joel
Publisher: W. W. Norton & Company
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Chapter 14, Problem 14.9P
Interpretation Introduction

(a)

Interpretation:

Based on the heat of hydrogenation, aromaticity of cyclopenta-1, 3-diene is to be determined.

Concept introduction:

The heat of hydrogenation depends on how many moles of H2 are required to completely hydrogenate the compound. The number of H2 moles required is equal to the number of double bonds present in the compound. This number of H2 moles can hydrogenate an equal number of moles of cyclohexene, releasing 120 kJ/mol.

If the difference between the calculated heat of hydrogenation and the measured heat of hydrogenation of a compound is comparable to the stabilization in benzene, about 150 kJ/mol, then the compound is aromatic. If it is much less than this, then the compound is nonaromatic.

Interpretation Introduction

(b)

Interpretation:

Based on the heat of hydrogenation, aromaticity of Naphthalene is to be determined.

Concept introduction:

The heat of hydrogenation depends on how many moles of H2 are required to completely hydrogenate the compound. The number of H2 moles required is equal to the number of double bonds present in the compound. This number of H2 moles can hydrogenate an equal number of moles of cyclohexene, releasing 120 kJ/mol.

If the difference between the calculated heat of hydrogenation and the measured heat of hydrogenation of a compound is comparable to the stabilization in benzene, about 150 kJ/mol, then the compound is aromatic. If it is much less than this, then the compound is nonaromatic.

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Chapter 14 Solutions

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)

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