a) Interpretation: The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given. Concept introduction: The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side, followed by the loss of a proton to give an anti addition product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents. To give: The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Question

Give mechanisms to account for the stereochemistry of the products observed fromthe addition of bromine to cis- and trans-but-2-ene (Figure 8-5). Why are two products formed from the cis isomer but only one from the trans? (Making models will behelpful.)

Answer 1

Question

Chapter 8.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side, followed by the loss of a proton to give an anti addition product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnikov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Interpretation Introduction

c)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

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Give mechanisms to account for the stereochemistry of the products observed fromthe addition of bromine to cis- and trans-but-2-ene (Figure 8-5). Why are two products formed from the cis isomer but only one from the trans? (Making models will behelpful.)

The solvolysis of 2-bromo-3-methylbutane potentially can give several products, includingboth E1 and SN1 products from both the unrearranged carbocation and the rearrangedcarbocation. Mechanisms 6-6 (page 282) and 7-2 (previous page) show the products fromthe rearranged carbocation. Summarize all the possible products, showing which carbocationthey come from and whether they are the products of E1 or SN1 reactions.

Answer Nos. 7-12 Only. Write only the product and the type of reaction it undergone. Thank you!

Answer 2

Question

Chapter 8.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side, followed by the loss of a proton to give an anti addition product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnikov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Interpretation Introduction

c)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Expert Solution & Answer

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Answer 3

Question

Chapter 8.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side, followed by the loss of a proton to give an anti addition product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnikov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Interpretation Introduction

c)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

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Answer 4

Question

Chapter 8.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side, followed by the loss of a proton to give an anti addition product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnikov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Interpretation Introduction

c)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

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Answer 5

Chapter 8.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side, followed by the loss of a proton to give an anti addition product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnikov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Interpretation Introduction

c)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Answer 6

Chapter 8.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side, followed by the loss of a proton to give an anti addition product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Answer 7

Chapter 8.SE, Problem 27MP

Interpretation Introduction

a)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side, followed by the loss of a proton to give an anti addition product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Answer 8

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnikov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Answer 9

Interpretation Introduction

b)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on the halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnikov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Answer 10

Interpretation Introduction

c)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Answer 11

Interpretation Introduction

c)

Interpretation:

The product of the reaction shown if the reaction was conducted in DMSO with water is to be given. The complete mechanism of the reaction including appropriate regiochemistry and stereochemistry is also to be given.

Concept introduction:

The addition of halogens to alkenes in the presence of aqueous DMSO results in the anti addition of the halohydrin, HOX, to the double bond. In the first step a cyclic halonium ion is formed by the attack of the double bond on halogen. In the second step water attacks the halonium ion from the least shielded side to give an anti addition product. The addition obeys Markovnokov orientation. The negative part (OH) adds to the doubly bonded carbon atom which has more number of substituents.

To give:

The product of the reaction shown if the reaction was conducted in DMSO with water and to give the complete mechanism of the reaction including appropriate regiochemistry and stereochemistry.

Answer 12

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Answer 23

Ch. 8.1 - Prob. 1P Ch. 8.1 - How many alkene products, including E,Z isomers,...Ch. 8.2 - Prob. 3P Ch. 8.2 - Addition of HCl to 1, 2-dimethylcyclohexene yields...Ch. 8.3 - Prob. 5P Ch. 8.3 - Prob. 6P Ch. 8.4 - Prob. 7P Ch. 8.4 - From what alkenes might the following alcohols...Ch. 8.5 - Prob. 9P Ch. 8.5 - What alkenes might be used to prepare the...

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