EBK ORGANIC CHEMISTRY-PRINT COMPANION (
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
Question
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Chapter 16, Problem 39PP

 (a)

Interpretation Introduction

Interpretation:

The given compounds are not participating as a diene in a Diels-Alder reaction should be explained.

Concept introduction:

  • The compounds having two C=C π bonds or C=C bond with C=O bonds are called dienes.

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.
  • Diels-Alder reaction is a [4+2] cycloaddition reaction, in which a π-system (conjugated) having four atoms (conjugated diene) and a π-system having two atoms (dienophile) are undergoing in cycloaddition reaction and producing a substituted cyclohexene.
  • Only the diene having s-cis conformation will undergo Diels-Alder reaction with dienophile.
  • The dienes shows conformations due to free rotation of CC bond. The conformations are s-cis and s-trans.

Example, the conformations for 1,3-butadiene are,

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 16, Problem 39PP , additional homework tip  1

Steric hindrance on the dienes prevents the s-cis conformations.

To explain: the given compounds are not participating as a diene in a Diels-Alder reaction.

(b)

Interpretation Introduction

Interpretation:

The given compounds are not participating as a diene in a Diels-Alder reaction should be explained.

Concept introduction:

  • The compounds having two C=C π bonds or C=C bond with C=O bonds are called dienes.

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.
  • Diels-Alder reaction is a [4+2] cycloaddition reaction, in which a π-system (conjugated) having four atoms (conjugated diene) and a π-system having two atoms (dienophile) are undergoing in cycloaddition reaction and producing a substituted cyclohexene.
  • Only the diene having s-cis conformation will undergo Diels-Alder reaction with dienophile.
  • The dienes shows conformations due to free rotation of CC bond. The conformations are s-cis and s-trans.

Example, the conformations for 1,3-butadiene are,

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 16, Problem 39PP , additional homework tip  2

Steric hindrance on the dienes prevents the s-cis conformations.

To explain: the given compounds are not participating as a diene in a Diels-Alder reaction.

(c)

Interpretation Introduction

Interpretation:

The given compounds are not participating as a diene in a Diels-Alder reaction should be explained.

Concept introduction:

  • The compounds having two C=C π bonds or C=C bond with C=O bonds are called dienes.

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.
  • Diels-Alder reaction is a [4+2] cycloaddition reaction, in which a π-system (conjugated) having four atoms (conjugated diene) and a π-system having two atoms (dienophile) are undergoing in cycloaddition reaction and producing a substituted cyclohexene.
  • Only the diene having s-cis conformation will undergo Diels-Alder reaction with dienophile.
  • The dienes shows conformations due to free rotation of CC bond. The conformations are s-cis and s-trans.

Example, the conformations for 1,3-butadiene are,

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 16, Problem 39PP , additional homework tip  3

Steric hindrance on the dienes prevents the s-cis conformations.

To explain: the given compounds are not participating as a diene in a Diels-Alder reaction.

(d)

Interpretation Introduction

Interpretation:

The given compounds are not participating as a diene in a Diels-Alder reaction should be explained.

Concept introduction:

  • The compounds having two C=C π bonds or C=C bond with C=O bonds are called dienes.

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.
  • Diels-Alder reaction is a [4+2] cycloaddition reaction, in which a π-system (conjugated) having four atoms (conjugated diene) and a π-system having two atoms (dienophile) are undergoing in cycloaddition reaction and producing a substituted cyclohexene.
  • Only the diene having s-cis conformation will undergo Diels-Alder reaction with dienophile.
  • The dienes shows conformations due to free rotation of CC bond. The conformations are s-cis and s-trans.

Example, the conformations for 1,3-butadiene are,

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 16, Problem 39PP , additional homework tip  4

Steric hindrance on the dienes prevents the s-cis conformations.

To explain: the given compounds are not participating as a diene in a Diels-Alder reaction.

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