The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown. Concept Introduction: Cope-rearrangement: It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form. Example with mechanism of cope-arrangement: In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state. Identification of cope-rearrangement in a 1 , 5 - d i e n e : In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C . Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here: The carbon atoms that are involving in the cope-rearrangement are shown in bold.

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Answer 1

Question

Chapter 20, Problem 20.53P

(a)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(b)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(c)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

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Diphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?

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The Wittig reaction can be used for the synthesis of conjugated dienes, as, for example, 1-phenyl-1,3-pentadiene. -CH=CHCH CHCH, 1-Phenyl-1,3-pentadiene Propose two sets of reagents that might be combined in a Wittig reaction to give this conjugated diene.

Answer 2

Question

Chapter 20, Problem 20.53P

(a)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(b)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(c)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

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Answer 3

Question

Chapter 20, Problem 20.53P

(a)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(b)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(c)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 20, Problem 20.53P

(a)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(b)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(c)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

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See solution

Answer 5

Chapter 20, Problem 20.53P

(a)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(b)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

(c)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

Answer 6

Chapter 20, Problem 20.53P

(a)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

Answer 7

Chapter 20, Problem 20.53P

(a)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

Answer 8

(b)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

Answer 9

(b)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

Answer 10

(c)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

Answer 11

(c)

Interpretation Introduction

Interpretation: The product formation in the given example of Cope rearrangement of 1,5-diene has to be shown.

Concept Introduction:

Cope-rearrangement:

It is a pericyclic reaction that involves the redistribution of six electrons through the formation of a cyclic transition state from which a 1,5-diene gets converted into its isomeric form.

Example with mechanism of cope-arrangement:

In this mechanism, two pi-bonds and one sigma bond of the reactant molecule has been rearranged and formed two new pi-bonds through a cyclic transition state.

Identification of cope-rearrangement in a1,5-diene:

In the cope-rearrangement, the flow of electrons takes place between six bonds that are bonded as C=C-C-C-C=C. Identification of such a bonding pattern in a 1,5-diene indicates the possibility of Cope rearrangement to occur as shown here:

The carbon atoms that are involving in the cope-rearrangement are shown in bold.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 20.1 - Prob. 20.1P Ch. 20.1 - Estimate the stabilization gained as a result of...Ch. 20.2 - Predict the product(s) formed by addition of one...Ch. 20.3 - Prob. 20.4P Ch. 20.3 - Prob. 20.5P Ch. 20.4 - Prob. 20.6P Ch. 20.5 - Prob. 20.7P Ch. 20.5 - Prob. 20.8P Ch. 20.5 - Prob. 20.9P Ch. 20.6 - Prob. 20.10P

Solution Summary: The author explains the pericyclic reaction of Cope rearrangement, which involves the redistribution of six electrons through the formation of a transition state from which the 1,5-diene

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Chapter 20 Solutions