ORGANIC CHEMISTRYPKGDRL+MLCRL MDL
ORGANIC CHEMISTRYPKGDRL+MLCRL MDL
3rd Edition
ISBN: 9781119416746
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 CHEMISTRYPKGDRL+MLCRL MDL, 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 CHEMISTRYPKGDRL+MLCRL MDL, 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 CHEMISTRYPKGDRL+MLCRL MDL, 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 CHEMISTRYPKGDRL+MLCRL MDL, 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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Chapter 16 Solutions

ORGANIC CHEMISTRYPKGDRL+MLCRL MDL

Ch. 16.5 - Prob. 9PTSCh. 16.5 - Prob. 10PTSCh. 16.5 - Prob. 11ATSCh. 16.5 - Prob. 12CCCh. 16.7 - Prob. 3LTSCh. 16.7 - Prob. 13PTSCh. 16.7 - Prob. 14ATSCh. 16.7 - Prob. 15CCCh. 16.7 - Prob. 16CCCh. 16.7 - Prob. 17CCCh. 16.7 - Predict the regiochemical outcome (major product)...Ch. 16.8 - Prob. 19CCCh. 16.9 - Prob. 20CCCh. 16.9 - Prob. 4LTSCh. 16.9 - Prob. 21PTSCh. 16.9 - Prob. 22ATSCh. 16.10 - Prob. 23CCCh. 16.10 - Prob. 24CCCh. 16.10 - Prob. 25CCCh. 16.10 - Prob. 26CCCh. 16.11 - Prob. 5LTSCh. 16.11 - Prob. 27PTSCh. 16.11 - Prob. 28ATSCh. 16.12 - Prob. 29CCCh. 16 - Prob. 30PPCh. 16 - Prob. 31PPCh. 16 - Prob. 32PPCh. 16 - Prob. 33PPCh. 16 - Prob. 34PPCh. 16 - Prob. 35PPCh. 16 - Prob. 36PPCh. 16 - Prob. 37PPCh. 16 - Prob. 38PPCh. 16 - Prob. 39PPCh. 16 - Prob. 40PPCh. 16 - Prob. 41PPCh. 16 - Prob. 42PPCh. 16 - Prob. 43PPCh. 16 - Prob. 44PPCh. 16 - Prob. 45PPCh. 16 - Prob. 46PPCh. 16 - Prob. 47PPCh. 16 - Prob. 48PPCh. 16 - Prob. 49PPCh. 16 - Prob. 50PPCh. 16 - Prob. 51PPCh. 16 - Prob. 52PPCh. 16 - Prob. 53PPCh. 16 - Prob. 54PPCh. 16 - Prob. 55PPCh. 16 - Prob. 56PPCh. 16 - Prob. 57PPCh. 16 - Prob. 58PPCh. 16 - Prob. 59PPCh. 16 - Prob. 60IPCh. 16 - Prob. 61IPCh. 16 - Prob. 62IPCh. 16 - Prob. 63IPCh. 16 - Prob. 64IPCh. 16 - Prob. 65IPCh. 16 - Prob. 66IPCh. 16 - Prob. 67IPCh. 16 - Prob. 68IPCh. 16 - Prob. 69IPCh. 16 - Prob. 70IPCh. 16 - Prob. 71IPCh. 16 - Prob. 72IPCh. 16 - Prob. 73IPCh. 16 - Prob. 74IPCh. 16 - Prob. 76IPCh. 16 - Prob. 77CPCh. 16 - Prob. 78CPCh. 16 - Prob. 79CPCh. 16 - Prob. 80CPCh. 16 - Prob. 81CP
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