Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 15, Problem 15.10P
Interpretation Introduction

(a)

Interpretation: The major product formed when given cycloalkane is heated with Br2 is to be drawn.

Concept introduction: Free radicals are classified as 1°, 2° or 3° depending upon the number of alkyl groups attached to it. The number of alkyl substituents increases, the stability of radical increases. This is due to the fact alkyl substituents donate their electrons to electron deficient radicals.

Halogens react with alkanes in presence of heat or light to form alkyl halides. This is known as halogenation reaction. This is a free radical substitution reaction. In this the halogen substitutes the hydrogen atom from CH sigma bond of the alkane.

Expert Solution
Check Mark

Answer to Problem 15.10P

The major product formed when given cycloalkane is heated with Br2 is shown below.

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  1

Explanation of Solution

The given species is,

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  2

Figure 1

Three types of radicals can be formed from cleavage of CH bond in the given molecule. Carbon atom highlighted produces 3° radical while the other carbon atoms of the cycloalkane produce 2° radical and methyl group produces 1° radical.

The number of alkyl substituents increases, the stability of radical increases. The order of stability is 1°<2°<3°. Higher the stability of the radical formed, weaker is the CH bond. The most stable radical is 3° radical. Hence, the major product formed is by the cleavage of 3°CH bond. The corresponding reaction is given below.

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  3

Figure 2

Conclusion

The major product formed when given cycloalkane is heated with Br2 is shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The major product formed when given cycloalkane is heated with Br2 is to be drawn.

Concept introduction: Free radicals are classified as 1°, 2° or 3° depending upon the number of alkyl groups attached to it. The number of alkyl substituents increases, the stability of radical increases. This is due to the fact alkyl substituents donate their electrons to electron deficient radicals.

Halogens react with alkanes in presence of heat or light to form alkyl halides. This is known as halogenation reaction. This is a free radical substitution reaction. In this the halogen substitutes the hydrogen atom from CH sigma bond of the alkane.

Expert Solution
Check Mark

Answer to Problem 15.10P

The major product formed when given cycloalkane is heated with Br2 is shown below.

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  4

Explanation of Solution

The given species is,

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  5

Figure 3

Three types of radicals can be formed from cleavage of CH bond in the given molecule. Carbon atom highlighted produces 3° radical while the other carbon atoms of the cycloalkane produce 2° radical and methyl group produces 1° radical.

The number of alkyl substituents increases, the stability of radical increases. The order of stability is 1°<2°<3°. Higher the stability of the radical formed, weaker is the CH bond. The most stable radical is 3° radical. Hence, the major product formed is by the cleavage of 3°CH bond. The corresponding reaction is given below.

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  6

Figure 4

Conclusion

The major product formed when given cycloalkane is heated with Br2 is shown in Figure 4.

Interpretation Introduction

(c)

Interpretation: The major product formed when given cycloalkane is heated with Br2 is to be drawn.

Concept introduction: Free radicals are classified as 1°, 2° or 3° depending upon the number of alkyl groups attached to it. The number of alkyl substituents increases, the stability of radical increases. This is due to the fact alkyl substituents donate their electrons to electron deficient radicals.

Halogens react with alkanes in presence of heat or light to form alkyl halides. This is known as halogenation reaction. This is a free radical substitution reaction. In this the halogen substitutes the hydrogen atom from CH sigma bond of the alkane.

Expert Solution
Check Mark

Answer to Problem 15.10P

The major product formed when given cycloalkane is heated with Br2 is shown below.

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  7

Explanation of Solution

The given species is,

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  8

Figure 5

Three types of radicals can be formed from cleavage of CH bond in the given molecule. Carbon atom highlighted produces 3° radical while the other carbon atoms of the cycloalkane produce 2° radical and methyl group produces 1° radical.

The number of alkyl substituents increases, the stability of radical increases. The order of stability is 1°<2°<3°. Higher the stability of the radical formed, weaker is the CH bond. The most stable radical is 3° radical. Hence, the major product formed is by the cleavage of 3°CH bond. The corresponding reaction is given below.

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  9

Figure 6

Conclusion

The major product formed when given cycloalkane is heated with Br2 is shown in Figure 6.

Interpretation Introduction

(c)

Interpretation: The major product formed when given cycloalkane is heated with Br2 is to be drawn.

Concept introduction: Free radicals are classified as 1°, 2° or 3° depending upon the number of alkyl groups attached to it. The number of alkyl substituents increases, the stability of radical increases. This is due to the fact alkyl substituents donate their electrons to electron deficient radicals.

Halogens react with alkanes in presence of heat or light to form alkyl halides. This is known as halogenation reaction. This is a free radical substitution reaction. In this the halogen substitutes the hydrogen atom from CH sigma bond of the alkane.

Expert Solution
Check Mark

Answer to Problem 15.10P

The major product formed when given cycloalkane is heated with Br2 is shown below.

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  10

Explanation of Solution

The given species is,

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  11

Figure 7

Two types of radicals can be formed from cleavage of CH bond in the given molecule. Carbon atoms of the cycloalkane produce 2° radical and methyl group produces 1° radical.

The number of alkyl substituents increases, the stability of radical increases. The order of stability is 1°<2°<3°. Higher the stability of the radical formed, weaker is the CH bond. The most stable radical is 3° radical. Hence, the major product formed is by the cleavage of 2°CH bond. The corresponding reaction is given below.

Organic Chemistry, Chapter 15, Problem 15.10P , additional homework tip  12

Figure 8

Conclusion

The major product formed when given cycloalkane is heated with Br2 is shown in Figure 8.

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Chapter 15 Solutions

Organic Chemistry

Ch. 15 - Prob. 15.11PCh. 15 - Synthesize each compound from (CH3)3CH. a....Ch. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Draw all constitutional isomers formed when each...Ch. 15 - Draw the structure of the four allylic halides...Ch. 15 - Which compounds can be prepared in good yield by...Ch. 15 - Which CH bond is most readily cleaved in linolenic...Ch. 15 - Prob. 15.23PCh. 15 - Draw the products formed when each alkene is...Ch. 15 - Problem 15.24 When adds to under radical...Ch. 15 - Prob. 15.26PCh. 15 - Draw an energy diagram for the two propagation...Ch. 15 - Prob. 15.28PCh. 15 - Problem 15.27 Draw the steps of the mechanism that...Ch. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Why is a benzylic CH bond labeled in red unusually...Ch. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - What alkane is needed to make each alkyl halide by...Ch. 15 - Which alkyl halides can be prepared in good yield...Ch. 15 - Prob. 15.41PCh. 15 - 15.40 Explain why radical bromination of p-xylene...Ch. 15 - a. What product(s) (excluding stereoisomers) are...Ch. 15 - Prob. 15.44PCh. 15 - Prob. 15.45PCh. 15 - Prob. 15.46PCh. 15 - 15.44 Draw all constitutional isomers formed when...Ch. 15 - Draw the organic products formed in each reaction....Ch. 15 - Prob. 15.49PCh. 15 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 15 - Prob. 15.51PCh. 15 - Prob. 15.52PCh. 15 - Prob. 15.53PCh. 15 - Prob. 15.54PCh. 15 - 15.53 Consider the following bromination: . a....Ch. 15 - 15.54 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 15.57PCh. 15 - An alternative mechanism for the propagation steps...Ch. 15 - Prob. 15.59PCh. 15 - Prob. 15.60PCh. 15 - Devise a synthesis of each compound from...Ch. 15 - Devise a synthesis of each target compound from...Ch. 15 - Devisea synthesis of each target compound from the...Ch. 15 - Devise a synthesis of each compound using CH3CH3...Ch. 15 - Prob. 15.65PCh. 15 - 15.63 As described in Section 9.16, the...Ch. 15 - 15.64 Ethers are oxidized with to form...Ch. 15 - Prob. 15.68PCh. 15 - Prob. 15.69PCh. 15 - 15.67 In cells, vitamin C exists largely as its...Ch. 15 - What monomer is needed to form each...Ch. 15 - Prob. 15.72PCh. 15 - Prob. 15.73PCh. 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. 15.76PCh. 15 - 15.74 A and B, isomers of molecular formula , are...Ch. 15 - Prob. 15.78PCh. 15 - Radical chlorination of CH3CH3 forms two minor...Ch. 15 - 15.76 Draw a stepwise mechanism for the...Ch. 15 - Prob. 15.81PCh. 15 - Prob. 15.82PCh. 15 - Prob. 15.83P
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