KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only
KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only
4th Edition
ISBN: 9781308429878
Author: 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,

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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.

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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,

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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.

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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,

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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.

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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,

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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.

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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,

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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.

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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,

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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.

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only, 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

KCTCS Organic Chemistry Value Edition (Looseleaf) - Text Only

Ch. 8 - Prob. 8.11PCh. 8 - What alkenes are formed from each alkyl halide by...Ch. 8 - Prob. 8.13PCh. 8 - Prob. 8.14PCh. 8 - Problem 8.15 How does each of the following...Ch. 8 - Prob. 8.16PCh. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Prob. 8.19PCh. 8 - Problem 8.19 Explain why...Ch. 8 - Prob. 8.21PCh. 8 - Draw the alkynes formed when each dihalide is...Ch. 8 - Prob. 8.23PCh. 8 - Draw a stepwise mechanism for the following...Ch. 8 - 8.24 Rank the alkenes shown in the ball-and-stick...Ch. 8 - Prob. 8.26PCh. 8 - 8.26 What is the major E2 elimination product...Ch. 8 - Prob. 8.28PCh. 8 - Prob. 8.29PCh. 8 - Prob. 8.30PCh. 8 - Prob. 8.31PCh. 8 - PGF2 is a prostaglandin, a group of compounds that...Ch. 8 - Prob. 8.33PCh. 8 - Prob. 8.34PCh. 8 - Prob. 8.35PCh. 8 - Prob. 8.36PCh. 8 - Prob. 8.37PCh. 8 - Prob. 8.38PCh. 8 - Prob. 8.39PCh. 8 - Prob. 8.40PCh. 8 - What alkene is the major product formed from each...Ch. 8 - Prob. 8.42PCh. 8 - Prob. 8.43PCh. 8 - Prob. 8.44PCh. 8 - 8.42 In the dehydrohalogenation of...Ch. 8 - Prob. 8.46PCh. 8 - Prob. 8.47PCh. 8 - Prob. 8.48PCh. 8 - Prob. 8.49PCh. 8 - Prob. 8.50PCh. 8 - Draw the products of each reaction. a.c. b.d.Ch. 8 - Draw the structure of a dihalide that could be...Ch. 8 - Under certain reaction conditions, 2,...Ch. 8 - For which reaction mechanisms, SN1, SN2, E1 or...Ch. 8 - Draw the organic products formed in each reaction....Ch. 8 - Prob. 8.56PCh. 8 - Prob. 8.57PCh. 8 - Draw all products, including stereoisomers, in...Ch. 8 - Draw all of the substitution and elimination...Ch. 8 - Prob. 8.60PCh. 8 - 8.59 Draw a stepwise, detailed mechanism for each...Ch. 8 - Draw the major product formed when...Ch. 8 - Draw a stepwise, detailed mechanism for the...Ch. 8 - Explain why the reaction of with gives ...Ch. 8 - Draw a stepwise detailed mechanism that...Ch. 8 - Prob. 8.66PCh. 8 - 8.65 Explain the selectivity observed in the...Ch. 8 - Prob. 8.68PCh. 8 - Although dehydrohalogenation occurs with anti...Ch. 8 - 8.68 (a) Draw all products formed by treatment of...
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