The compounds are not optically active, the reason 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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Answer 1

Question

Chapter 8.14, Problem 46P

a)

Interpretation Introduction

Interpretation: The compounds are not optically active, the reason 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 order of diene reactivity 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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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

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.

Highlight the chirality (or stereogenic) center(s) in the given compound. A compound may have one or more stereogenic centers. OH OH OH OH OH OH

Answer 2

Question

Chapter 8.14, Problem 46P

a)

Interpretation Introduction

Interpretation: The compounds are not optically active, the reason 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 order of diene reactivity 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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Answer 3

Question

Chapter 8.14, Problem 46P

a)

Interpretation Introduction

Interpretation: The compounds are not optically active, the reason 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 order of diene reactivity 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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Answer 4

Question

Chapter 8.14, Problem 46P

a)

Interpretation Introduction

Interpretation: The compounds are not optically active, the reason 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 order of diene reactivity 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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Answer 5

Chapter 8.14, Problem 46P

a)

Interpretation Introduction

Interpretation: The compounds are not optically active, the reason 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 order of diene reactivity 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.

Answer 6

Chapter 8.14, Problem 46P

a)

Interpretation Introduction

Interpretation: The compounds are not optically active, the reason 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.

Answer 7

Chapter 8.14, Problem 46P

a)

Interpretation Introduction

Interpretation: The compounds are not optically active, the reason 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.

Answer 8

b)

Interpretation Introduction

Interpretation: The order of diene reactivity 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.

Answer 9

b)

Interpretation Introduction

Interpretation: The order of diene reactivity 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.

Answer 10

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Answer 11

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Answer 13

Ch. 8.1 - Prob. 1P Ch. 8.1 - Prob. 2P Ch. 8.4 - Prob. 3P Ch. 8.5 - Prob. 4P Ch. 8.5 - Prob. 6P Ch. 8.6 - a. Predict the relative bond lengths of the three...Ch. 8.6 - Prob. 8P Ch. 8.6 - Prob. 9P Ch. 8.6 - Prob. 10P Ch. 8.7 - Prob. 11P

Solution Summary: The author explains Diels-Alder reaction, where two reactants form a cyclic product.

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