ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 15, Problem 15.18P

Draw all constitutional isomers formed when each alkene is treated with NBS + h v .

a.Chapter 15, Problem 15.18P, Draw all constitutional isomers formed when each alkene is treated with .
a.		b.	c. 
 , example  1 b.Chapter 15, Problem 15.18P, Draw all constitutional isomers formed when each alkene is treated with .
a.		b.	c. 
 , example  2 c. Chapter 15, Problem 15.18P, Draw all constitutional isomers formed when each alkene is treated with .
a.		b.	c. 
 , example  3

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The constitutional isomer formed by the reaction of given alkene with NBS+hv is to be drawn.

Concept introduction: The reaction of alkene with Nbromosuccinimide in presence of light results in the formation of allylic halide. NBS is the source of Br2. Allylic halogenation results in the formation of two product mixture. Abstraction of hydrogen from allylic carbon result in the formation of a resonance stabilized radical. These two resonance structures react with Br2 to form constitutional isomers as products.

Answer to Problem 15.18P

The constitutional isomers formed by the reaction of given alkene with NBS+hv are,

ORGANIC CHEMISTRY, Chapter 15, Problem 15.18P , additional homework tip  1

Explanation of Solution

The reaction of alkene with Nbromosuccinimide in presence of light results in the formation of allylic halide. NBS is the source of Br2. Allylic halogenation results in the formation of two product mixture. Abstraction of hydrogen from allylic carbon result in the formation of a resonance stabilized radical. These two resonance structures react with Br2 to form constitutional isomers as products.

The given alkene is shown below.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.18P , additional homework tip  2

Figure 1

The general steps involved in the reaction of allylic bromination with NBS are stated below.

• The first step is the initiation of bromine radical.

• The next step is the propagation in which generation of allylic radical take place.

• In third step, allylic radical reacts with Br2 to form allylic halide.

The constitutional isomer formed by the reaction of given alkene with NBS+hv are shown below.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.18P , additional homework tip  3

Figure 2

Therefore, the constitutional isomers formed for the given reaction are 1bromobut2ene and 3bromobut1ene.

Conclusion

The constitutional isomers formed by the reaction of given alkene with NBS+hv are shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The constitutional isomer formed by the reaction of given alkene with NBS+hv is to be drawn.

Concept introduction: The reaction of alkene with Nbromosuccinimide in presence of light results in the formation of allylic halide. NBS is the source of Br2. Allylic halogenation results in the formation of two product mixture. Abstraction of hydrogen from allylic carbon result in the formation of a resonance stabilized radical. These two resonance structures react with Br2 to form constitutional isomers as products.

Answer to Problem 15.18P

The constitutional isomers formed by the reaction of given alkene with NBS+hv are,

ORGANIC CHEMISTRY, Chapter 15, Problem 15.18P , additional homework tip  4

Explanation of Solution

The reaction of alkene with Nbromosuccinimide in presence of light results in the formation of allylic halide. NBS is the source of Br2. Allylic halogenation results in the formation of two product mixture. Abstraction of hydrogen from allylic carbon result in the formation of a resonance stabilized radical. These two resonance structures react with Br2 to form constitutional isomers as products.

The given alkene is shown below.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.18P , additional homework tip  5

Figure 3

The general steps involved in the reaction of allylic bromination with NBS are stated below.

• The first step is the initiation of bromine radical.

• The next step is the propagation in which generation of allylic radical take place.

• In third step, allylic radical reacts with Br2 to form allylic halide.

The constitutional isomer formed by the reaction of given alkene with NBS+hv are shown below.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.18P , additional homework tip  6

Figure 4

Therefore, the constitutional isomers formed for the given reaction are 6bromo3,3dimethylcyclohex1ene and 3bromo4,4dimethylcyclohex1ene.

Conclusion

The constitutional isomers formed by the reaction of given alkene with NBS+hv are shown in Figure 4.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The constitutional isomer formed by the reaction of given alkene with NBS+hv is to be drawn.

Concept introduction: The reaction of alkene with Nbromosuccinimide in presence of light results in the formation of allylic halide. NBS is the source of Br2. Allylic halogenation results in the formation of two product mixture. Abstraction of hydrogen from allylic carbon result in the formation of a resonance stabilized radical. These two resonance structures react with Br2 to form constitutional isomers as products.

Answer to Problem 15.18P

The constitutional isomers formed by the reaction of given alkene with NBS+hv are,

ORGANIC CHEMISTRY, Chapter 15, Problem 15.18P , additional homework tip  7

Explanation of Solution

The reaction of alkene with Nbromosuccinimide in presence of light results in the formation of allylic halide. NBS is the source of Br2. Allylic halogenation results in the formation of two product mixture. Abstraction of hydrogen from allylic carbon result in the formation of a resonance stabilized radical. These two resonance structures react with Br2 to form constitutional isomers as products.

The given alkene is shown below.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.18P , additional homework tip  8

Figure 5

The general steps involved in the reaction of allylic bromination with NBS are stated below.

• The first step is the initiation of bromine radical.

• The next step is the propagation in which generation of allylic radical take place.

• In third step, allylic radical reacts with Br2 to form allylic halide.

The constitutional isomer formed by the reaction of given alkene with NBS+hv are shown below.

ORGANIC CHEMISTRY, Chapter 15, Problem 15.18P , additional homework tip  9

Figure 6

Therefore, the constitutional isomers formed for the given reaction are 3bromo2ethylbut1ene and 3(bromoethyl)pent2ene.

Conclusion

The constitutional isomers formed by the reaction of given alkene with NBS+hv are shown in Figure 6.

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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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