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

a) Fill in the following reaction scheme by drawing the structure of intermediate 3 and products 4-5. Chemical formulas have been added as guidance. H3C CI H2SO4 H2N. CH3 2 C6H11NO3 C5H9NO3 CH3OH CH3 1 - HCI 3 H20 4 Step 1 Step 2 H2N CH3 N' HO. C3H17N304 Assign the absolute stereochemistry of the stereogenic centre in compound 1.

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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a) Fill in the following reaction scheme by drawing the structure of intermediate 3 and products 4-5. Chemical formulas have been added as guidance. H3C CI H2SO4 H2N. CH3 2 C6H11NO3 C5H9NO3 CH3OH CH3 1 - HCI 3 H20 4 Step 1 Step 2 H2N CH3 N' HO. C3H17N304 Assign the absolute stereochemistry of the stereogenic centre in compound 1.

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.

8. Predict the products of the following reactions and propose a complete mechanism for each reaction. 1 Hg(OAc). CH;OH, 2 NABH, CH, CH,CH,CH=CH, 1. BH3. THF 2. H,O». OH

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.

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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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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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