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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Students have asked these similar questions

Following are example of Cope rearrangements of 1,5-dienes. Show that product can be formed in a single step by a mechanism involving redistribution of six electrons in a cyclic transition state

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?

Determine all of the products obtained from the addition of HCl to the 1,3-diene. Once determined, draw a mechanism that accounts for the formation of every product. Then, Identify and account for the formation of the major adduct/or adducts under these conditions assuming that the reaction is conducted under thermodynamic conditions.

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.

Expert Solution & Answer

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Check out a sample textbook solution

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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