Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 16, Problem 16.51P
Interpretation Introduction

(a)

Interpretation: The diene and dienophile that are needed to prepare given product is to be stated.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Expert Solution
Check Mark

Answer to Problem 16.51P

The diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  1

Explanation of Solution

The given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  2

Figure 1

Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Retro synthesis can be carried out to identify the diene and dienophile for the given product.

Therefore, the diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  3

Figure 2

Conclusion

The diene and dienophile that are needed to prepare given product are shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The diene and dienophile that are needed to prepare given product is to be stated.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Expert Solution
Check Mark

Answer to Problem 16.51P

The diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  4

Explanation of Solution

The given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  5

Figure 3

Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Retro synthesis can be carried out to identify the diene and dienophile for the given product.

Therefore, the diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  6

Figure 4

Conclusion

The diene and dienophile that are needed to prepare given product are shown in Figure 4.

Interpretation Introduction

(c)

Interpretation: The diene and dienophile that are needed to prepare given product is to be stated.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Expert Solution
Check Mark

Answer to Problem 16.51P

The diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  7

Explanation of Solution

The given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  8

Figure 5

Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Retro synthesis can be carried out to identify the diene and dienophile for the given product.

Therefore, the diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  9

Figure 6

Conclusion

The diene and dienophile that are needed to prepare given product are shown in Figure 6.

Interpretation Introduction

(d)

Interpretation: The diene and dienophile that are needed to prepare given product is to be stated.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Expert Solution
Check Mark

Answer to Problem 16.51P

The diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  10

Explanation of Solution

The given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  11

Figure 7

Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Retro synthesis can be carried out to identify the diene and dienophile for the given product.

Therefore, the diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  12

Figure 8

Conclusion

The diene and dienophile that are needed to prepare given product are shown in Figure 8.

Interpretation Introduction

(e)

Interpretation: The diene and dienophile that are needed to prepare given product is to be stated.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Expert Solution
Check Mark

Answer to Problem 16.51P

The diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  13

Explanation of Solution

The given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  14

Figure 9

Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Retro synthesis can be carried out to identify the diene and dienophile for the given product.

Therefore, the diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  15

Figure 10

Conclusion

The diene and dienophile that are needed to prepare given product are shown in Figure 10.

Interpretation Introduction

(f)

Interpretation: The diene and dienophile that are needed to prepare given product is to be stated.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Expert Solution
Check Mark

Answer to Problem 16.51P

The diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  16

Explanation of Solution

The given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  17

Figure 11

Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Retro synthesis can be carried out to identify the diene and dienophile for the given product.

Therefore, the diene and dienophile that are needed to prepare given product is shown below.

Organic Chemistry, Chapter 16, Problem 16.51P , additional homework tip  18

Figure 12

Conclusion

The diene and dienophile that are needed to prepare given product are shown in Figure 12.

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Chapter 16 Solutions

Organic Chemistry

Ch. 16 - Problem 16.12 Using hybridization, predict how the...Ch. 16 - Problem 16.13 Use resonance theory to explain why...Ch. 16 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.17PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.19PCh. 16 - Prob. 16.20PCh. 16 - Rank the following dienophiles in order of...Ch. 16 - Prob. 16.22PCh. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.27PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Prob. 16.32PCh. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Explain each statement using resonance theory. a....Ch. 16 - 16.37 Draw the structure of each compound. a. in...Ch. 16 - Draw and name all dienes of molecular formula...Ch. 16 - Prob. 16.39PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.41PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.43PCh. 16 - 16.43 Treatment of alkenes A and B with gives the...Ch. 16 - 16.44 Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.46PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - Prob. 16.53PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.55PCh. 16 - Prob. 16.56PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.58PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Draw the products of each reaction. Indicate the...Ch. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - 16.65 The treatment of isoprene with one...Ch. 16 - 16.66 The treatment of with forms B (molecular...Ch. 16 - Rank the following compounds in the order of...Ch. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74P
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