ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 15, Problem 15.57P

Devise a synthesis of each compound from cyclopentane and any other required organic or inorganic reagents.

a. Chapter 15, Problem 15.57P, 15.57 Devise a synthesis of each compound from cyclopentane and any other required organic or , example  1 b. Chapter 15, Problem 15.57P, 15.57 Devise a synthesis of each compound from cyclopentane and any other required organic or , example  2 c. Chapter 15, Problem 15.57P, 15.57 Devise a synthesis of each compound from cyclopentane and any other required organic or , example  3 d. Chapter 15, Problem 15.57P, 15.57 Devise a synthesis of each compound from cyclopentane and any other required organic or , example  4 e. Chapter 15, Problem 15.57P, 15.57 Devise a synthesis of each compound from cyclopentane and any other required organic or , example  5

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is to be stated.

Concept introduction: Alkenes undergo bromination reaction at primary, secondary and tertiary carbon atom through free radical mechanism on reaction with Br2 in the presence of light or heat. However, alkenes undergo bromination at allylic carbon atom on reaction with Br2 in the presence of light or heat.

Answer to Problem 15.57P

The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is,

ORGANIC CHEMISTRY, Chapter 15, Problem 15.57P , additional homework tip  1

Figure 1

Explanation of Solution

Cyclopentane is used as a starting material and it converts into bromocyclopentane on treatment with Br2 in the presence of light or heat. The bromine group is converted into hydroxyl group when bromocyclopentane is treated with KOH. The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is shown in Figure 1.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.57P , additional homework tip  2

Figure 1

Conclusion

The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is shown in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is to be stated.

Concept introduction: Alkenes undergo bromination reaction at primary, secondary and tertiary carbon atom through free radical mechanism on reaction with Br2 in the presence of light or heat. However, alkenes undergo bromination at allylic carbon atom on reaction with Br2 in the presence of light or heat.

Answer to Problem 15.57P

The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is,

ORGANIC CHEMISTRY, Chapter 15, Problem 15.57P , additional homework tip  3

Figure 2

Explanation of Solution

In the first step, cyclopentane undergoes bromination when it is treated with Br2 in the presence of light or heat. In the next step, bromine atom is eliminated from bromocyclopentane to form cyclopentane in the presence of tert-butoxide. The desired product is formed when cyclopentene reacts with m-chloroperbenzoic acid (mCPBA) as shown in Figure 2.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.57P , additional homework tip  4

Figure 2

Conclusion

The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is to be stated.

Concept introduction: Alkenes undergo bromination reaction at primary, secondary and tertiary carbon atom through free radical mechanism on reaction with Br2 in the presence of light or heat. However, alkenes undergo bromination at allylic carbon atom on reaction with Br2 in the presence of light or heat.

Answer to Problem 15.57P

The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is,

ORGANIC CHEMISTRY, Chapter 15, Problem 15.57P , additional homework tip  5

Figure 3

Explanation of Solution

In the first step, cyclopentane undergoes bromination when it is treated with Br2 in the presence of light or heat. In the next step, bromine atom is eliminated from bromocyclopentane to form cyclopentane in the presence of tert-butoxide. Cyclopentene then undergoes bromination at allylic position on reaction with NBS in presence of light followed by addition reaction with Br2 to give desired product as shown in Figure 3.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.57P , additional homework tip  6

Figure 3

Conclusion

The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is shown in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is to be stated.

Concept introduction: Alkenes undergo bromination reaction at primary, secondary and tertiary carbon atom through free radical mechanism on reaction with Br2 in the presence of light or heat. However, alkenes undergo bromination at allylic carbon atom on reaction with Br2 in the presence of light or heat.

Answer to Problem 15.57P

The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is,

ORGANIC CHEMISTRY, Chapter 15, Problem 15.57P , additional homework tip  7

Figure 4

Explanation of Solution

In the first step, cyclopentane undergoes bromination when it is treated with Br2 in the presence of light or heat. In the next step, bromine atom is eliminated from bromocyclopentane to form cyclopentane in the presence of tert-butoxide. Cyclopentene then undergoes bromination at allylic position on reaction with NBS in presence of light. The bromine group is converted into hydroxyl group when this product is treated with KOH. This leads to the formation of desired product as shown in Figure 4.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.57P , additional homework tip  8

Figure 4

Conclusion

The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is shown in Figure 4.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is to be stated.

Concept introduction: Alkenes undergo bromination reaction at primary, secondary and tertiary carbon atom through free radical mechanism on reaction with Br2 in the presence of light or heat. However, alkenes undergo bromination at allylic carbon atom on reaction with Br2 in the presence of light or heat.

Answer to Problem 15.57P

The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is,

ORGANIC CHEMISTRY, Chapter 15, Problem 15.57P , additional homework tip  9

Figure 5

Explanation of Solution

In the first step, cyclopentane undergoes bromination when it is treated with Br2 in the presence of light or heat. In the next step, bromine atom is eliminated from bromocyclopentane to form cyclopentane in the presence of tert-butoxide. Cyclopentene then undergoes addition reaction with Br2 to give 1,2-dibromocyclopentane. In the next two steps, bromine atom is converted into nitrile and hydroxyl group on reaction with KCN and KOH, respectively, which leads to the formation of desired product.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.57P , additional homework tip  10

Figure 5

Conclusion

The synthesis of given compound from cyclopentane by the use of any other organic or inorganic reagent is shown in Figure 5.

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Chapter 15 Solutions

ORGANIC CHEMISTRY

Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Draw the products of each reaction. a. b. c. Ch. 15 - Draw all constitutional isomers formed when each...Ch. 15 - Draw the structure of the four allylic halides...Ch. 15 - Problem 15.20 Which compounds can be prepared in...Ch. 15 - Which CH bond is most readily cleaved in linolenic...Ch. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Problem 15.24 When adds to under radical...Ch. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Problem 15.27 Draw the steps of the mechanism that...Ch. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - 15.35 What is the major monobromination product...Ch. 15 - Prob. 15.36PCh. 15 - 15.37 What alkane is needed to make each alkyl...Ch. 15 - 15.38 Which alkyl halides can be prepared in good...Ch. 15 - Prob. 15.39PCh. 15 - 15.40 Explain why radical bromination of p-xylene...Ch. 15 - a. What product(s) (excluding stereoisomers) are...Ch. 15 - Prob. 15.42PCh. 15 - 15.43 Draw the products formed when each alkene is...Ch. 15 - 15.44 Draw all constitutional isomers formed when...Ch. 15 - 15.45 Draw the organic products formed in each...Ch. 15 - Prob. 15.46PCh. 15 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 15 - 15.48 Draw the products formed in each reaction...Ch. 15 - Prob. 15.49PCh. 15 - 15.50 Draw all the monochlorination products that...Ch. 15 - Prob. 15.51PCh. 15 - 15.52 (a) Draw the products (including...Ch. 15 - 15.53 Consider the following bromination: . a....Ch. 15 - 15.54 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 15.55PCh. 15 - Prob. 15.56PCh. 15 - 15.57 Devise a synthesis of each compound from...Ch. 15 - Prob. 15.58PCh. 15 - Prob. 15.59PCh. 15 - 15.60 Devise a synthesis of each compound using ...Ch. 15 - Prob. 15.61PCh. 15 - Prob. 15.62PCh. 15 - 15.63 As described in Section 9.16, the...Ch. 15 - 15.64 Ethers are oxidized with to form...Ch. 15 - Prob. 15.65PCh. 15 - Prob. 15.66PCh. 15 - 15.67 In cells, vitamin C exists largely as its...Ch. 15 - What monomer is needed to form each...Ch. 15 - Prob. 15.69PCh. 15 - Prob. 15.70PCh. 15 - 15.71 Draw a stepwise mechanism for the following...Ch. 15 - 15.72 As we will learn in Chapter 30, styrene...Ch. 15 - Prob. 15.73PCh. 15 - 15.74 A and B, isomers of molecular formula , are...Ch. 15 - Prob. 15.75PCh. 15 - 15.76 Draw a stepwise mechanism for the...Ch. 15 - Prob. 15.77PCh. 15 - Prob. 15.78PCh. 15 - Prob. 15.79P
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