The mistake made in procedure that might result in appearance of unusual red-orange solid should be identified. 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 results 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. The bromination of ( E ) - C i n n a m i c a c i d yields four stereoisomers illustrated as follows:

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Answer 1

Question

Chapter 10.6, Problem 24E

Interpretation Introduction

Interpretation:The mistake made in procedure that might result in appearance of unusual red-orange solid should be identified.

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 results 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.

The bromination of (E)-Cinnamic acid

yields four stereoisomers illustrated as follows:

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Answer 2

Question

Chapter 10.6, Problem 24E

Interpretation Introduction

Interpretation:The mistake made in procedure that might result in appearance of unusual red-orange solid should be identified.

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 results 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.

The bromination of (E)-Cinnamic acid

yields four stereoisomers illustrated as follows:

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Answer 3

Question

Chapter 10.6, Problem 24E

Interpretation Introduction

Interpretation:The mistake made in procedure that might result in appearance of unusual red-orange solid should be identified.

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 results 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.

The bromination of (E)-Cinnamic acid

yields four stereoisomers illustrated as follows:

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Answer 4

Question

Chapter 10.6, Problem 24E

Interpretation Introduction

Interpretation:The mistake made in procedure that might result in appearance of unusual red-orange solid should be identified.

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 results 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.

The bromination of (E)-Cinnamic acid

yields four stereoisomers illustrated as follows:

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Answer 5

Chapter 10.6, Problem 24E

Interpretation Introduction

Interpretation:The mistake made in procedure that might result in appearance of unusual red-orange solid should be identified.

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 results 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.

The bromination of (E)-Cinnamic acid

yields four stereoisomers illustrated as follows:

Answer 6

Chapter 10.6, Problem 24E

Interpretation Introduction

Interpretation:The mistake made in procedure that might result in appearance of unusual red-orange solid should be identified.

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 results 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.

The bromination of (E)-Cinnamic acid

yields four stereoisomers illustrated as follows:

Answer 7

Chapter 10.6, Problem 24E

Interpretation Introduction

Interpretation:The mistake made in procedure that might result in appearance of unusual red-orange solid should be identified.

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 results 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.

The bromination of (E)-Cinnamic acid

yields four stereoisomers illustrated as follows:

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 the mechanism of Br_2 addition by electrophilic addition reaction, which results in a three-membered bromonium ion intermediate.

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