(a) Interpretation: The allowed and reasonable sigmatropic reaction can account for the given reaction is to be stated. Concept introduction: The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π − system to another region takes place simultaneously.

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Answer 1

Question

Chapter 28, Problem 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

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Students have asked these similar questions

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.

Compound A has molecular formula C4H10, and gives two monochlorides, B and C, on photochemical chlorination. Treatment of either of these monochlorides with potassium tert-butoxide gives the same alkene (C4H8) as the product, but B leads to just one isomer of the alkene, D, where C gives D and another isomer of the alkene, E. Treatment of monochlorides B and C with aqueous ethanol gives products F and G, respectively, both of which are of molecular formula C4H10O. What are the names of compounds A-G?

Complete the following by drawing products for a and b, and also identify the diene and dienophile in each one.

Answer 2

Question

Chapter 28, Problem 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

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Answer 3

Question

Chapter 28, Problem 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

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Answer 4

Question

Chapter 28, Problem 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

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Answer 5

Chapter 28, Problem 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Answer 6

Chapter 28, Problem 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Answer 7

Chapter 28, Problem 28.19P

Interpretation Introduction

(a)

Interpretation:

The allowed and reasonable sigmatropic reaction can account for the given reaction is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The expected product from a similar reaction of 2,3−dimethyl−1,3−cyclopentadiene is to be stated.

Concept introduction:

The pericyclic reactions in which one sigma bond is converted to another sigma bond within the uncatalyzed intramolecular reaction are known as sigmatropic reactions. In this rearrangement, the shifting of one substituent from one region of a π− system to another region takes place simultaneously.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 28 - Prob. 28.1P Ch. 28 - Prob. 28.2P Ch. 28 - Prob. 28.3P Ch. 28 - Prob. 28.4P Ch. 28 - Prob. 28.5P Ch. 28 - Prob. 28.6P Ch. 28 - Prob. 28.7P Ch. 28 - Prob. 28.8P Ch. 28 - Prob. 28.9P Ch. 28 - Prob. 28.10P

Solution Summary: The author explains that the allowed and reasonable sigmatropic reaction can account for the given reaction.

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Chapter 28 Solutions