The mechanism for the reaction of ( E ) -cinnamic acid and bromine should be proposed. 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

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Chapter 10.6, Problem 22E

Interpretation Introduction

Interpretation:The mechanism for the reaction of (E)-cinnamic acid and bromine should be proposed.

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.

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Answer 2

Question

Chapter 10.6, Problem 22E

Interpretation Introduction

Interpretation:The mechanism for the reaction of (E)-cinnamic acid and bromine should be proposed.

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.

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Answer 3

Question

Chapter 10.6, Problem 22E

Interpretation Introduction

Interpretation:The mechanism for the reaction of (E)-cinnamic acid and bromine should be proposed.

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.

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Answer 4

Question

Chapter 10.6, Problem 22E

Interpretation Introduction

Interpretation:The mechanism for the reaction of (E)-cinnamic acid and bromine should be proposed.

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.

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Answer 5

Chapter 10.6, Problem 22E

Interpretation Introduction

Interpretation:The mechanism for the reaction of (E)-cinnamic acid and bromine should be proposed.

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 6

Chapter 10.6, Problem 22E

Interpretation Introduction

Interpretation:The mechanism for the reaction of (E)-cinnamic acid and bromine should be proposed.

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 22E

Interpretation Introduction

Interpretation:The mechanism for the reaction of (E)-cinnamic acid and bromine should be proposed.

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

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Answer 9

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Answer 10

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Answer 11

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 explains that the mechanism for the reaction of (E)-cinnamic acid and bromine should be proposed.

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