Structural formulae for the alkene that gives the indicated product should be drawn. 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.For example in cases of cyclohexene mechanistic pathway that occurs is illustrated below.

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Answer 1

Question

Chapter 10.6, Problem 4E

(a)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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 cyclohexene mechanistic pathway that occurs is illustrated below.

(b)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

(c)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

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Draw the products formed when alkene reacts with these reagents: (i) H2 in the presence of Pd catalyst, (ii) HCl.

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When propene reacts with gaseous hydrogen bromide, HBr, two products, 1-bromopropane and 2-bromopropane are formed. The reaction is a two-step process in which the electrophilic attack occurs in the first step. Identify the electrophile in this reaction Draw a diagram showing the first step of the reaction that leads to the production of 2-bromopropane.

Answer 2

Question

Chapter 10.6, Problem 4E

(a)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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 cyclohexene mechanistic pathway that occurs is illustrated below.

(b)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

(c)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

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Answer 3

Question

Chapter 10.6, Problem 4E

(a)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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 cyclohexene mechanistic pathway that occurs is illustrated below.

(b)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

(c)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

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Answer 4

Question

Chapter 10.6, Problem 4E

(a)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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 cyclohexene mechanistic pathway that occurs is illustrated below.

(b)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

(c)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

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Answer 5

Chapter 10.6, Problem 4E

(a)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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 cyclohexene mechanistic pathway that occurs is illustrated below.

(b)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

(c)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

Answer 6

Chapter 10.6, Problem 4E

(a)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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 cyclohexene mechanistic pathway that occurs is illustrated below.

Answer 7

Chapter 10.6, Problem 4E

(a)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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 cyclohexene mechanistic pathway that occurs is illustrated below.

Answer 8

(b)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

Answer 9

(b)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

Answer 10

(c)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

Answer 11

(c)

Interpretation Introduction

Interpretation: Structural formulae for the alkene that gives the indicated product should be drawn.

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.

Answer 12

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Answer 13

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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 explains the structure of the alkene that gives the indicated product.

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