Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written. Concept introduction: Alkenes are considered electron-rich and undergo bromination addition reaction with Br 2 in presence of CCl 4 by electrophilic addition reaction. The mechanism of Br 2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br 2 and this result in attack of Br + on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate. In the second step, the strained bromonium ion intermediate opens while Br − attack from behind the electron-deficient carbon analogous to S N 2 attack.

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Answer 1

Question

Chapter 10.6, Problem 2E

(a)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

(b)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

(c)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of Br2 to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack. For example, in cases of the trans-stilbene mechanistic pathway that occurs for addition bromine water is illustrated below.

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(a 4 shows scanning electron microscope (SEM) images of extruded actions of packing bed for two capillary columns of different diameters, al 750 (bottom image) and b) 30-μm-i.d. Both columns are packed with the same stationary phase, spherical particles with 1-um diameter. A) When the columns were prepared, the figure shows that the column with the larger diameter has more packing irregularities. Explain this observation. B) Predict what affect this should have on band broadening and discuss your prediction using the van Deemter terms. C) Does this figure support your explanations in application question 33? Explain why or why not and make any changes in your answers in light of this figure. Figure 4 SEM images of sections of packed columns for a) 750 and b) 30-um-i.d. capillary columns.³

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Answer 2

Question

Chapter 10.6, Problem 2E

(a)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

(b)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

(c)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of Br2 to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack. For example, in cases of the trans-stilbene mechanistic pathway that occurs for addition bromine water is illustrated below.

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Answer 3

Question

Chapter 10.6, Problem 2E

(a)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

(b)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

(c)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of Br2 to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack. For example, in cases of the trans-stilbene mechanistic pathway that occurs for addition bromine water is illustrated below.

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Answer 4

Question

Chapter 10.6, Problem 2E

(a)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

(b)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

(c)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of Br2 to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack. For example, in cases of the trans-stilbene mechanistic pathway that occurs for addition bromine water is illustrated below.

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Answer 5

Chapter 10.6, Problem 2E

(a)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

(b)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

(c)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of Br2 to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack. For example, in cases of the trans-stilbene mechanistic pathway that occurs for addition bromine water is illustrated below.

Answer 6

Chapter 10.6, Problem 2E

(a)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

Answer 7

Chapter 10.6, Problem 2E

(a)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

Answer 8

(b)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

Answer 9

(b)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of HBr to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack.

Answer 10

(c)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of Br2 to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack. For example, in cases of the trans-stilbene mechanistic pathway that occurs for addition bromine water is illustrated below.

Answer 11

(c)

Interpretation Introduction

Interpretation: Structure of the major product expected from the ionic addition of Br2 to the substrate indicated should be written.

Concept introduction:Alkenes are considered electron-rich and undergo bromination addition reaction with Br2 in presence of CCl4 by electrophilic addition reaction.

The mechanism of Br2 addition occurs in two steps. In the first step, nucleophilic olefin abstracts the electrophilic bromine atom from Br2 and this result in attack of Br+ on the electron-rich olefinic bond that forms a sigma bond to each end of the olefinic bond. Such interaction leads to a three-membered bromonium ion intermediate.

In the second step, the strained bromonium ion intermediate opens while Br− attack from behind the electron-deficient carbon analogous to SN2 attack. For example, in cases of the trans-stilbene mechanistic pathway that occurs for addition bromine water is illustrated below.

Answer 12

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Answer 15

Ch. 10.2 - Prob. 1E Ch. 10.2 - Prob. 2E Ch. 10.2 - Prob. 3E Ch. 10.2 - Prob. 4E Ch. 10.2 - Prob. 5E Ch. 10.2 - Prob. 6E Ch. 10.2 - Prob. 7E Ch. 10.2 - Prob. 8E Ch. 10.2 - Prob. 9E Ch. 10.2 - Prob. 10E

Solution Summary: The author illustrates the structure of the major product expected from the ionic addition of HBr to the substrate indicated.

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