Pearson eText Organic Chemistry -- Instant Access (Pearson+)
Pearson eText Organic Chemistry -- Instant Access (Pearson+)
8th Edition
ISBN: 9780135213711
Author: Paula Bruice
Publisher: PEARSON+
Question
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Chapter 8.15, Problem 47P

a)

Interpretation Introduction

Interpretation: The diene and dienophile from the given compounds has to be predicted.

Concept Introduction:

Diels-Alder reaction:

A conjugated diene reacts with a compound containing a carbon-carbon double bond.  It is a cycloaddition reaction, where two reactants form a cyclic product.

Conformation of Diene:

S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.

S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.

Condition for Diels-Alder reaction:

The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.

b)

Interpretation Introduction

Interpretation: The diene and dienophile from the given compounds has to be predicted.

Concept Introduction:

Diels-Alder reaction:

A conjugated diene reacts with a compound containing a carbon-carbon double bond.  It is a cycloaddition reaction, where two reactants form a cyclic product.

Conformation of Diene:

S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.

S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.

Condition for Diels-Alder reaction:

The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.

c)

Interpretation Introduction

Interpretation: The diene and dienophile from the given compounds has to be predicted.

Concept Introduction:

Diels-Alder reaction:

A conjugated diene reacts with a compound containing a carbon-carbon double bond.  It is a cycloaddition reaction, where two reactants form a cyclic product.

Conformation of Diene:

S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.

S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.

Condition for Diels-Alder reaction:

The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.

d)

Interpretation Introduction

Interpretation: The diene and dienophile from the given compounds to be predicted.

Concept Introduction:

Diels-Alder reaction:

A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.

Conformation of Diene:

S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.

S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.

Condition for Diels-Alder reaction:

The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.

e)

Interpretation Introduction

Interpretation: The diene and dienophile from the given compounds has to be predicted.

Concept Introduction:

Diels-Alder reaction:

A conjugated diene reacts with a compound containing a carbon-carbon double bond. It is a cycloaddition reaction, where two reactants form a cyclic product.

Conformation of Diene:

S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.

S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.

Condition for Diels-Alder reaction:

The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.

f)

Interpretation Introduction

Interpretation: The diene and dienophile from the given compounds has to be predicted.

Concept Introduction:

Diels-Alder reaction:

A conjugated diene reacts with a compound containing a carbon-carbon double bond.  It is a cycloaddition reaction, where two reactants form a cyclic product.

Conformation of Diene:

S-Cis Conformer: The double bonds are cis about the single bond (s stands for single), in an s-cis conformer.

S-trans Conformer: The double bonds are trans- about the single bond (s stands for single) in an s-trans conformer.

Condition for Diels-Alder reaction:

The conjugate diene must be in an s-cis conformation because when it is in an S-trans conformation, C-1 and C-4 are too far apart to react with the dienophile in a concerted reaction.

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Chapter 8 Solutions

Pearson eText Organic Chemistry -- Instant Access (Pearson+)

Ch. 8.7 - Prob. 12PCh. 8.7 - Prob. 13PCh. 8.8 - Prob. 14PCh. 8.8 - Prob. 15PCh. 8.8 - Prob. 16PCh. 8.9 - Which member of each pair is the stronger acid?Ch. 8.9 - Which member of each pair is the stronger base? a....Ch. 8.9 - Rank the following compounds from strongest acid...Ch. 8.10 - Prob. 20PCh. 8.10 - Which acid in each of the following pairs is...Ch. 8.10 - Prob. 23PCh. 8.11 - Prob. 24PCh. 8.11 - Prob. 26PCh. 8.12 - Prob. 27PCh. 8.12 - Prob. 28PCh. 8.12 - Prob. 29PCh. 8.12 - Prob. 30PCh. 8.12 - Prob. 31PCh. 8.12 - Prob. 32PCh. 8.13 - Prob. 33PCh. 8.13 - Prob. 34PCh. 8.13 - Prob. 35PCh. 8.13 - What are the major 1,2- and 1,4-addition products...Ch. 8.13 - Prob. 38PCh. 8.14 - Prob. 39PCh. 8.14 - Prob. 40PCh. 8.14 - Prob. 41PCh. 8.14 - Prob. 42PCh. 8.14 - Prob. 43PCh. 8.14 - Prob. 44PCh. 8.14 - Prob. 46PCh. 8.15 - Prob. 47PCh. 8.17 - Prob. 48PCh. 8.17 - Prob. 49PCh. 8.18 - Prob. 50PCh. 8.18 - Prob. 52PCh. 8.18 - Prob. 53PCh. 8.18 - Prob. 54PCh. 8.19 - Prob. 55PCh. 8.20 - Prob. 56PCh. 8.20 - What orbitals contain the electrons represented as...Ch. 8.20 - Prob. 59PCh. 8.20 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - Prob. 65PCh. 8 - Prob. 66PCh. 8 - Prob. 67PCh. 8 - Prob. 68PCh. 8 - Prob. 69PCh. 8 - Prob. 70PCh. 8 - Prob. 71PCh. 8 - Prob. 72PCh. 8 - Prob. 73PCh. 8 - Which compound is the strongest base?Ch. 8 - Prob. 75PCh. 8 - Prob. 76PCh. 8 - a. The A ring (Section 3.16) of cortisone (a...Ch. 8 - Prob. 78PCh. 8 - Prob. 79PCh. 8 - Prob. 80PCh. 8 - Prob. 81PCh. 8 - Purine is a heterocyclic compound with four...Ch. 8 - Prob. 83PCh. 8 - Why is the delocalization energy of pyrrole (21...Ch. 8 - Prob. 85PCh. 8 - Prob. 86PCh. 8 - Prob. 87PCh. 8 - A student obtained two products from the reaction...Ch. 8 - Prob. 89PCh. 8 - a. How could each of the following compounds be...Ch. 8 - Draw the products obtained from the reaction of...Ch. 8 - How would the following substituents affect the...Ch. 8 - Prob. 93PCh. 8 - The acid dissociation constant (Ka) for loss of a...Ch. 8 - Protonated cyclohexylamine has a Ka = 1 1011...Ch. 8 - Draw the product or products that would be...Ch. 8 - Prob. 97PCh. 8 - Prob. 98PCh. 8 - Prob. 99PCh. 8 - Prob. 100PCh. 8 - Prob. 101PCh. 8 - a. Propose n mechanism for the following reaction:...Ch. 8 - Prob. 103PCh. 8 - As many as 18 different Diels-Alder products can...Ch. 8 - Prob. 105PCh. 8 - Prob. 106PCh. 8 - Prob. 107PCh. 8 - Prob. 108PCh. 8 - The experiment shown next and discussed in Section...Ch. 8 - Prob. 110PCh. 8 - Prob. 111PCh. 8 - Prob. 112PCh. 8 - Prob. 1PCh. 8 - Prob. 2PCh. 8 - Prob. 3PCh. 8 - Prob. 4PCh. 8 - Prob. 5PCh. 8 - Prob. 6PCh. 8 - Prob. 7PCh. 8 - Prob. 8PCh. 8 - Prob. 9PCh. 8 - Prob. 10PCh. 8 - Prob. 11PCh. 8 - Prob. 12P
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