Organic Chemistry
Organic Chemistry
3rd Edition
ISBN: 9781119316152
Author: Klein, David R.
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, 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, 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, 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, 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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2) (4 pt) After the reaction was completed, the student collected the following data. Crude product data is the data collected after the reaction is finished, but before the product is purified. "Pure" product data is the data collected after attempted purification using recrystallization. Student B's data: Crude product data "Pure" product data after recrystallization Crude mass: 0.93 g grey solid Crude mp: 96-106 °C Crude % yield: Pure mass: 0.39 g white solid Pure mp: 111-113 °C Pure % yield: a) Calculate the crude and pure percent yields for the student's reaction. b) Summarize what is indicated by the crude and pure melting points.
Don't used hand raiting
Don't used hand raiting

Chapter 16 Solutions

Organic Chemistry

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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