EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
4th Edition
ISBN: 9781119659525
Author: Klein
Publisher: WILEY CONS
Question
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Chapter 16.2, Problem 4CC

(a)

Interpretation Introduction

Interpretation:

From the given isomeric dienes, the compound liberating least heat and the compound liberating most heat upon hydrogenations with 2 moles of hydrogen gases are needed to be identified.

Concept introduction:

  • The heat liberation in a reaction is depends upon the stability of the reactant compounds. If the reactant compound is more stable, then the heat liberation will be less.

Based on the proximity of C=C bonds in dienes, they are classified into three.

  • Cumulated dienes: the C=C bonds are located adjacent carbons.
  • Conjugated dienes: the C=C bonds or C=C and C=O are separated by one σ-bond.
  • Isolated dienes: the C=C bonds are separated by two or more σ-bonds.
  • The conjugated dienes are more stable as compare to isolated dienes because the delocalization of π bonds is taking place, so this forms some stabilization energy in conjugated system.
  • The more substituted alkenes are more stable as compared to less substituted alkenes. Because the more alkyl group attachment to a double bond make it more stable due to the +I effect of alkyl groups. It means the alkyl groups will push electrons towards the double bonded carbon atoms, so the double bond becomes strengthened and highly stabilized

To identify: the compound liberating least heat and the compound liberating most heat upon hydrogenations with 2 moles of hydrogen gases from the given isomeric dienes.

(b)

Interpretation Introduction

Interpretation:

From the given isomeric dienes, the compound liberating least heat and the compound liberating most heat upon hydrogenations with 2 moles of hydrogen gases are needed to be identified.

Concept introduction:

  • The heat liberation in a reaction is depends upon the stability of the reactant compounds. If the reactant compound is more stable, then the heat liberation will be less.

Based on the proximity of C=C bonds in dienes, they are classified into three.

  • Cumulated dienes: the C=C bonds are located adjacent carbons.
  • Conjugated dienes: the C=C bonds or C=C and C=O are separated by one σ-bond.
  • Isolated dienes: the C=C bonds are separated by two or more σ-bonds.
  • The conjugated dienes are more stable as compare to isolated dienes because the delocalization of π bonds is taking place, so this forms some stabilization energy in conjugated system.
  • The more substituted alkenes are more stable as compared to less substituted alkenes. Because the more alkyl group attachment to a double bond make it more stable due to the +I effect of alkyl groups. It means the alkyl groups will push electrons towards the double bonded carbon atoms, so the double bond becomes strengthened and highly stabilized

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