Organic Chemistry, Third Edition Binder Ready Version
Organic Chemistry, Third Edition Binder Ready Version
3rd Edition
ISBN: 9781119110453
Author: Klein
Publisher: WILEY
Question
Book Icon
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, Third Edition Binder Ready Version, 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, Third Edition Binder Ready Version, 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, Third Edition Binder Ready Version, 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, Third Edition Binder Ready Version, 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.

Blurred answer
Students have asked these similar questions
Identify the starting material in the following reaction. Click the "draw structure" button to launch the drawing utility. draw structure ... [1] 0 3 C10H18 [2] CH3SCH3 H
In an equilibrium mixture of the formation of ammonia from nitrogen and hydrogen, it is found that PNH3 = 0.147 atm, PN2 = 1.41 atm and Pн2 = 6.00 atm. Evaluate Kp and Kc at 500 °C. 2 NH3 (g) N2 (g) + 3 H₂ (g) K₂ = (PN2)(PH2)³ = (1.41) (6.00)³ = 1.41 x 104
What alkene or alkyne yields the following products after oxidative cleavage with ozone? Click the "draw structure" button to launch the drawing utility. and two equivalents of CH2=O draw structure ...

Chapter 16 Solutions

Organic Chemistry, Third Edition Binder Ready Version

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
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY