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

Q4: Rank the relative nucleophilicity of halide ions in water solution and DMF solution, respectively. F CI Br | Q5: Determine which of the substrates will and will not react with NaSCH3 in an SN2 reaction to have a reasonable yield of product. NH2 Br Br Br OH Br

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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Q4: Rank the relative nucleophilicity of halide ions in water solution and DMF solution, respectively. F CI Br | Q5: Determine which of the substrates will and will not react with NaSCH3 in an SN2 reaction to have a reasonable yield of product. NH2 Br Br Br OH Br

Q7: Rank the following groups in order of basicity, nucleophilicity, and leaving group ability. a) H₂O, OH, CH3COOT b) NH3, H₂O, H₂S

Q8: Rank the following compounds in order of increasing reactivity in a nucleophilic substitution reaction with CN as the nucleophile. Br A B NH2 LL F C D OH CI LLI E Q9: Complete the missing entities for following reactions (e.g., major product(s), reactants, and/or solvents) for the SN2 reactions to occur efficiently. Include curved-arrow mechanism for reactions a) to d). a) H "Cl D + -OCH 3 Page 3 of 5

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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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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