(a) Interpretation: The increasing order of S N 1 − E 1 reaction of the given compounds along with the reason is to be stated. Concept introduction: The S N 1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in S N 1 and E 1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In S N 1 pathway, the next step is substitution while in E 1 pathway, the next step is elimination.According to Zaitsev rule, in E 1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

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Answer 1

Question

Chapter 18, Problem 18.3P

Interpretation Introduction

(a)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

Interpretation Introduction

(b)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

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(a) Give a mechanism for this reaction, showing how the two products arise as aconsequence of the resonance-stabilized intermediate.(b) The bromination of cyclohexene using NBS gives only one major product, as shown onthe previous page. Explain why there is no second product from an allylic shift.

(a) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomericproducts are formed. Give their structures, and label each asymmetric carbon atomas (R) or (S). What is the relationship between these isomers?(b) Repeat part (a) for (E)-3-methylhex-3-ene. What is the relationship between the productsformed from (Z)-3-methylhex-3-ene and those formed from (E)-3-methylhex-3-ene?

(ii) The elimination reaction between 2-bromobutane and NaOCH2CH3 gives two organic products. Draw a mechanism for the reaction which produces the major organic elimination product and provide a rationale as to why that is the major product.

Answer 2

Question

Chapter 18, Problem 18.3P

Interpretation Introduction

(a)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

Interpretation Introduction

(b)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

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Answer 3

Question

Chapter 18, Problem 18.3P

Interpretation Introduction

(a)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

Interpretation Introduction

(b)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

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Answer 4

Question

Chapter 18, Problem 18.3P

Interpretation Introduction

(a)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

Interpretation Introduction

(b)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

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Answer 5

Chapter 18, Problem 18.3P

Interpretation Introduction

(a)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

Interpretation Introduction

(b)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

Answer 6

Chapter 18, Problem 18.3P

Interpretation Introduction

(a)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

Answer 7

Chapter 18, Problem 18.3P

Interpretation Introduction

(a)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The increasing order of SN1−E1 reaction of the given compounds along with the reason is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction. The first step is common in SN1 and E1 reactions i.e. the heterolysis of carbon halogen bond to form a carbocation. In SN1 pathway, the next step is substitution while in E1 pathway, the next step is elimination.According to Zaitsev rule, in E1 reactions, the more substituted or more alkylated alkene is the major product as it is more stable.

Answer 10

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Answer 13

Ch. 18 - Prob. 18.1P Ch. 18 - Prob. 18.2P Ch. 18 - Prob. 18.3P Ch. 18 - Prob. 18.4P Ch. 18 - Prob. 18.5P Ch. 18 - Prob. 18.6P Ch. 18 - Prob. 18.7P Ch. 18 - Prob. 18.8P Ch. 18 - Prob. 18.9P Ch. 18 - Prob. 18.10P

Solution Summary: The author explains the increasing order of S_TextN1- TextE1, which depends on the stability of carbocation and the leaving group ability.

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Chapter 18 Solutions