a) Interpretation: To predict the product of the reaction given. Concept introduction: Alkenes can be converted into alcohols by the hydroboration-oxidation reaction. The reaction occurs with syn stereochemistry following anti-Markovnikov regiochemistry. To predict: The product of the reaction given.

Question

1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.

Answer 1

Question

Chapter 17.3, Problem 6P

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be converted into alcohols by the hydroboration-oxidation reaction. The reaction occurs with syn stereochemistry following anti-Markovnikov regiochemistry.

To predict:

The product of the reaction given.

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be hydrated using oxymercuration-demercuration process. The reaction occurs following Markonikov regiochemistry yielding a more highly substituted alcohol as the product.

To predict:

The product of the reaction given.

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Hydroxylation with O_sO₄ takes place with syn stereochemistry through the formation of a cyclic osmate intermediate formed by the addition of O_sO₄ to the double bond in alkene. The cyclic osmate gets cleaved when treated with NaHSO₃ to give a cis diol as the product.

To predict:

The product of the reaction given.

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1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.

3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in the reactant before being able to draw the arrows corresponding to product formation. A. B. Rearrangement ΘΗ

2. Draw the arrows required to make the following reactions occur. Please ensure your arrows point from exactly where you want to exactly where you want. If it is unclear from where arrows start or where they end, only partial credit will be given. Note: You may need to draw in lone pairs before drawing the arrows. A. B. H-Br 人 C Θ CI H Cl Θ + Br O

Answer 2

Question

Chapter 17.3, Problem 6P

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be converted into alcohols by the hydroboration-oxidation reaction. The reaction occurs with syn stereochemistry following anti-Markovnikov regiochemistry.

To predict:

The product of the reaction given.

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be hydrated using oxymercuration-demercuration process. The reaction occurs following Markonikov regiochemistry yielding a more highly substituted alcohol as the product.

To predict:

The product of the reaction given.

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Hydroxylation with O_sO₄ takes place with syn stereochemistry through the formation of a cyclic osmate intermediate formed by the addition of O_sO₄ to the double bond in alkene. The cyclic osmate gets cleaved when treated with NaHSO₃ to give a cis diol as the product.

To predict:

The product of the reaction given.

Expert Solution & Answer

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Answer 3

Question

Chapter 17.3, Problem 6P

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be converted into alcohols by the hydroboration-oxidation reaction. The reaction occurs with syn stereochemistry following anti-Markovnikov regiochemistry.

To predict:

The product of the reaction given.

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be hydrated using oxymercuration-demercuration process. The reaction occurs following Markonikov regiochemistry yielding a more highly substituted alcohol as the product.

To predict:

The product of the reaction given.

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Hydroxylation with O_sO₄ takes place with syn stereochemistry through the formation of a cyclic osmate intermediate formed by the addition of O_sO₄ to the double bond in alkene. The cyclic osmate gets cleaved when treated with NaHSO₃ to give a cis diol as the product.

To predict:

The product of the reaction given.

Expert Solution & Answer

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Answer 4

Question

Chapter 17.3, Problem 6P

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be converted into alcohols by the hydroboration-oxidation reaction. The reaction occurs with syn stereochemistry following anti-Markovnikov regiochemistry.

To predict:

The product of the reaction given.

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be hydrated using oxymercuration-demercuration process. The reaction occurs following Markonikov regiochemistry yielding a more highly substituted alcohol as the product.

To predict:

The product of the reaction given.

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Hydroxylation with O_sO₄ takes place with syn stereochemistry through the formation of a cyclic osmate intermediate formed by the addition of O_sO₄ to the double bond in alkene. The cyclic osmate gets cleaved when treated with NaHSO₃ to give a cis diol as the product.

To predict:

The product of the reaction given.

Expert Solution & Answer

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Answer 5

Chapter 17.3, Problem 6P

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be converted into alcohols by the hydroboration-oxidation reaction. The reaction occurs with syn stereochemistry following anti-Markovnikov regiochemistry.

To predict:

The product of the reaction given.

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be hydrated using oxymercuration-demercuration process. The reaction occurs following Markonikov regiochemistry yielding a more highly substituted alcohol as the product.

To predict:

The product of the reaction given.

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Hydroxylation with O_sO₄ takes place with syn stereochemistry through the formation of a cyclic osmate intermediate formed by the addition of O_sO₄ to the double bond in alkene. The cyclic osmate gets cleaved when treated with NaHSO₃ to give a cis diol as the product.

To predict:

The product of the reaction given.

Answer 6

Chapter 17.3, Problem 6P

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be converted into alcohols by the hydroboration-oxidation reaction. The reaction occurs with syn stereochemistry following anti-Markovnikov regiochemistry.

To predict:

The product of the reaction given.

Answer 7

Chapter 17.3, Problem 6P

Interpretation Introduction

a)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be converted into alcohols by the hydroboration-oxidation reaction. The reaction occurs with syn stereochemistry following anti-Markovnikov regiochemistry.

To predict:

The product of the reaction given.

Answer 8

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be hydrated using oxymercuration-demercuration process. The reaction occurs following Markonikov regiochemistry yielding a more highly substituted alcohol as the product.

To predict:

The product of the reaction given.

Answer 9

Interpretation Introduction

b)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Alkenes can be hydrated using oxymercuration-demercuration process. The reaction occurs following Markonikov regiochemistry yielding a more highly substituted alcohol as the product.

To predict:

The product of the reaction given.

Answer 10

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Hydroxylation with O_sO₄ takes place with syn stereochemistry through the formation of a cyclic osmate intermediate formed by the addition of O_sO₄ to the double bond in alkene. The cyclic osmate gets cleaved when treated with NaHSO₃ to give a cis diol as the product.

To predict:

The product of the reaction given.

Answer 11

Interpretation Introduction

c)

Interpretation:

To predict the product of the reaction given.

Concept introduction:

Hydroxylation with O_sO₄ takes place with syn stereochemistry through the formation of a cyclic osmate intermediate formed by the addition of O_sO₄ to the double bond in alkene. The cyclic osmate gets cleaved when treated with NaHSO₃ to give a cis diol as the product.

To predict:

The product of the reaction given.

Answer 12

Expert Solution & Answer

Answer 13

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Answer 14

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Answer 17

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Answer 18

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Answer 19

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Answer 23

Ch. 17.1 - Give IUPAC names for the following compounds:Ch. 17.1 - Prob. 2P Ch. 17.2 - The following data for isomeric four-carbon...Ch. 17.2 - Rank the following substances in order of...Ch. 17.2 - Prob. 5P Ch. 17.3 - Prob. 6P Ch. 17.4 - What reagent would you use to accomplish each of...Ch. 17.4 - Prob. 8P Ch. 17.5 - Prob. 9P Ch. 17.5 - Prob. 10P

Solution Summary: The author explains that alkenes can be converted into alcohols by the hydroboration-oxidation reaction. The product of the reaction is 2-methyl-3-pentanol.

Chapter 17 Solutions