Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 8, Problem 8.35P
Interpretation Introduction

(a)

Interpretation: All constitutional isomers formed in the given E2 reaction are to be drawn and the major product by the use of Zaitsev rule is to be predicted.

Concept introduction: The removal of halide and neighboring β hydrogen atom in the presence of strong base leads to the formation of alkene. The mechanism followed by the reaction is E2. According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction.

Expert Solution
Check Mark

Answer to Problem 8.35P

All constitutional isomers formed in the given E2 reaction are,

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  1

Explanation of Solution

The E2 elimination reaction involves the removal of halide and neighboring β hydrogen atom in the presence of strong base which leads to the formation of alkene. Carbon atom on which halogen is present is known as α carbon atom. Carbon atom attached to α carbon atom is known as β carbon atom and hydrogen atoms attached to it are termed as β hydrogen atoms.

In the given compound, two β hydrogen atoms are present. The E2 elimination reaction of given compound gives two constitutional isomers as shown in Figure 2.

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  2

Figure 1

According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction. Therefore, disubstituted alkene is the major product of the reaction.

Conclusion

The product formed in the given reaction is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation: All constitutional isomers formed in the given E2 reaction are to be drawn and the major product by the use of Zaitsev rule is to be predicted.

Concept introduction: The removal of halide and neighboring β hydrogen atom in the presence of strong base leads to the formation of alkene. The mechanism followed by the reaction is E2. According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction.

Expert Solution
Check Mark

Answer to Problem 8.35P

All constitutional isomers formed in the given E2 reaction are,

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  3

Explanation of Solution

The E2 elimination reaction involves the removal of halide and neighboring β hydrogen atom in the presence of strong base which leads to the formation of alkene. Carbon atom on which halogen is present is known as α carbon atom. Carbon atom attached to α carbon atom is known as β carbon atom and hydrogen atoms attached to it are termed as β hydrogen atoms.

In the given compound, only one β hydrogen atom is present. The E2 elimination reaction of given compound gives one monosubstituted product as shown in Figure 4.

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  4

Figure 2

According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction. Therefore, monosubstituted alkene is the major product of the reaction.

Conclusion

The product formed in the given reaction is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation: All constitutional isomers formed in the given E2 reaction are to be drawn and the major product by the use of Zaitsev rule is to be predicted.

Concept introduction: The removal of halide and neighboring β hydrogen atom in the presence of strong base leads to the formation of alkene. The mechanism followed by the reaction is E2. According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction.

Expert Solution
Check Mark

Answer to Problem 8.35P

All constitutional isomers formed in the given E2 reaction are,

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  5

Explanation of Solution

The E2 elimination reaction involves the removal of halide and neighboring β hydrogen atom in the presence of strong base which leads to the formation of alkene. Carbon atom on which halogen is present is known as α carbon atom. Carbon atom attached to α carbon atom is known as β carbon atom and hydrogen atoms attached to it are termed as β hydrogen atoms.

In the given compound, three β hydrogen atoms are present. The E2 elimination reaction of given compound gives three constitutional isomers as shown in Figure 6.

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  6

Figure 3

According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction. Therefore, tetrasubstituted alkene is the major product of the reaction.

Conclusion

The product formed in the given reaction is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation: All constitutional isomers formed in the given E2 reaction are to be drawn and the major product by the use of Zaitsev rule is to be predicted.

Concept introduction: The removal of halide and neighboring β hydrogen atom in the presence of strong base leads to the formation of alkene. The mechanism followed by the reaction is E2. According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction.

Expert Solution
Check Mark

Answer to Problem 8.35P

All constitutional isomers formed in the given E2 reaction are,

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  7

Explanation of Solution

In the given compound, only one β hydrogen atom is present. Therefore, only one elimination product is possible as shown below.

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  8

Figure 4

Conclusion

The product formed in the given reaction is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation: All constitutional isomers formed in the given E2 reaction are to be drawn and the major product by the use of Zaitsev rule is to be predicted.

Concept introduction: The removal of halide and neighboring β hydrogen atom in the presence of strong base leads to the formation of alkene. The mechanism followed by the reaction is E2. According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction.

Expert Solution
Check Mark

Answer to Problem 8.35P

All constitutional isomers formed in the given E2 reaction are,

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  9

Explanation of Solution

The E2 elimination reaction involves the removal of halide and neighboring β hydrogen atom in the presence of strong base which leads to the formation of alkene. Carbon atom on which halogen is present is known as α carbon atom. Carbon atom attached to α carbon atom is known as β carbon atom and hydrogen atoms attached to it are termed as β hydrogen atoms.

In the given compound, two β hydrogen atoms are present. The E2 elimination reaction of given compound gives two constitutional isomers as shown in Figure 8.

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  10

Figure 5

According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction.

Conclusion

The product formed in the given reaction is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation: All constitutional isomers formed in the given E2 reaction are to be drawn and the major product by the use of Zaitsev rule is to be predicted.

Concept introduction: The removal of halide and neighboring β hydrogen atom in the presence of strong base leads to the formation of alkene. The mechanism followed by the reaction is E2. According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction.

Expert Solution
Check Mark

Answer to Problem 8.35P

All constitutional isomers formed in the given E2 reaction are,

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  11.

Explanation of Solution

The E2 elimination reaction involves the removal of halide and neighboring β hydrogen atom in the presence of strong base which leads to the formation of alkene. Carbon atom on which halogen is present is known as α carbon atom. Carbon atom attached to α carbon atom is known as β carbon atom and hydrogen atoms attached to it are termed as β hydrogen atoms.

In the given compound, two β hydrogen atoms are present. The E2 elimination reaction of given compound gives two constitutional isomers as shown in Figure 8.

Organic Chemistry, Chapter 8, Problem 8.35P , additional homework tip  12

Figure 6

According to Zaitsev rule, more substituted alkene is obtained as a major product in E2 elimination reaction. Therefore, trisubstituted alkene is the major product of the reaction.

Conclusion

All constitutional isomers formed in the given E2 reaction are shown in Figure 6. Trisubstituted alkene is the major product of the reaction.

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Chapter 8 Solutions

Organic Chemistry

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