Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 27, Problem 27.52P

Draw the products of each reaction.

a.Chapter 27, Problem 27.52P, 27.52	Draw the products of each reaction.

	c. 
	d. 
 , example  1 c. Chapter 27, Problem 27.52P, 27.52	Draw the products of each reaction.

	c. 
	d. 
 , example  2

b.Chapter 27, Problem 27.52P, 27.52	Draw the products of each reaction.

	c. 
	d. 
 , example  3 d. Chapter 27, Problem 27.52P, 27.52	Draw the products of each reaction.

	c. 
	d. 
 , example  4

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The product formed for the given reaction is to be drawn.

Concept introduction: Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Answer to Problem 27.52P

The product formed for the given reaction is Cyclooct4enone shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  1

Explanation of Solution

The given reaction is shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  2

Figure 1

The product formed for the given reaction is shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  3

Figure 2

In the given reaction, curved arrows shows the movement of pi bonds to give the final product. In this type of reaction, the compound undergoes to the [3,3] sigmatropic rearrangement in which old sigma bond breaks and results in the formation of new sigma bonds to give the desired product.

Thus, the name of product formed is Cyclooct4enone.

Conclusion

The product formed for the given reaction is Cyclooct4enone.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The product formed for the given reaction is to be drawn.

Concept introduction: Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Answer to Problem 27.52P

The product formed for the given reaction is Bicyclo[5.3.1]undec3en11one shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  4

Explanation of Solution

The given reaction is shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  5

Figure 3

The product formed for the given reaction is shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  6

Figure 4

The first step in the given reaction is the formation of enolate ion. The curved arrows show the movement of pi bonds to give the final product. In the next step, the compound undergoes to the [3,3] sigmatropic rearrangement in which old sigma bond breaks and results in the formation of new sigma bonds to give the desired product.

Thus, the product formed for the given reaction is Bicyclo[5.3.1]undec3en11one.

Conclusion

The product formed for the given reaction is Bicyclo[5.3.1]undec3en11one.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The product formed for the given reaction is to be drawn.

Concept introduction: Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Answer to Problem 27.52P

The product formed for the given reaction is 2(2methylenecyclohexyl)phenol shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  7

Explanation of Solution

The given reaction is shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  8

Figure 5

The product formed for the given reaction is shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  9

Figure 6

In the given reaction, curved arrows shows the movement of pi bonds to give the final product. In this type of reaction, the compound undergoes to the [3,3] sigmatropic rearrangement in which old sigma bond breaks and results in the formation of new sigma bonds to give the desired product.

Thus, the name of product formed is 2(2methylenecyclohexyl)phenol.

Conclusion

The product formed for the given reaction is 2(2methylenecyclohexyl)phenol.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The product formed for the given reaction is to be drawn.

Concept introduction:

Answer to Problem 27.52P

The product formed for the given reaction is,

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  10

Explanation of Solution

The given reaction is shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  11

Figure 7

The molecular formula of the product is C7H8.

The product formed for the given reaction is shown below.

Organic Chemistry, Chapter 27, Problem 27.52P , additional homework tip  12

Figure 8

The given reactant undergoes [2+2] cycloaddition reaction to give the desired product.

Conclusion

The product formed for the given reaction is shown in Figure 8.

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Chapter 27 Solutions

Organic Chemistry

Ch. 27 - Problem 27.11 What product would be formed by the...Ch. 27 - Consider cycloheptatrienone and ethylene, and draw...Ch. 27 - Problem 27.13 Show that a thermal suprafacial...Ch. 27 - Prob. 27.14PCh. 27 - a Draw the product of the following [4+2]...Ch. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Problem 27.18 Using orbital symmetry, explain why...Ch. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Prob. 27.21PCh. 27 - Prob. 27.22PCh. 27 - Prob. 27.23PCh. 27 - Prob. 27.24PCh. 27 - Problem 27.25 (a) What product is formed by the...Ch. 27 - Prob. 27.26PCh. 27 - Prob. 27.27PCh. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - Prob. 27.30PCh. 27 - Prob. 27.31PCh. 27 - Prob. 27.32PCh. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - Prob. 27.35PCh. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - Prob. 27.39PCh. 27 - Prob. 27.40PCh. 27 - 27.41 What starting materials are needed to...Ch. 27 - Prob. 27.42PCh. 27 - Prob. 27.43PCh. 27 - Prob. 27.44PCh. 27 - Prob. 27.45PCh. 27 - Prob. 27.46PCh. 27 - 27.47 What product is formed from the [5,5]...Ch. 27 - Prob. 27.48PCh. 27 - 27.49 Draw structures for A, B, and C in the...Ch. 27 - Prob. 27.50PCh. 27 - Prob. 27.51PCh. 27 - 27.52 Draw the products of each reaction. c....Ch. 27 - Prob. 27.53PCh. 27 - 27.54 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.55PCh. 27 - Prob. 27.56PCh. 27 - Prob. 27.57PCh. 27 - 27.58 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.59PCh. 27 - Prob. 27.60PCh. 27 - Prob. 27.61PCh. 27 - Prob. 27.62PCh. 27 - Prob. 27.63P
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