ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
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,

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, 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,

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, 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,

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, 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,

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, 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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Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.
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