The structure of the major product formed from alkene indicated should be predicted. Concept introduction: Hydroboration-oxidation involves the sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes . Hydroboration is essentially the addition of H − and BH 2 across the alkene. For example, the reaction between BH 3 and alkene to form syn-products illustrated as follows: The mechanistic pathway can be illustrated as follows: In the first step one equivalent of BH 3 is added across the C − C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH 3 .

Question

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Answer 1

Question

Chapter 10.8, Problem 8E

(a)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves the sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(a)

Expert Solution

Explanation of Solution

The hydroboration-oxidation productis illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 4

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Since carbon 1 is less substituted thus OH must add to this carbon while H to other olefin carbon in accordance with anti-Markovnikov’s Rule.

(b)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(b)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 8

Anti-Markovnikov’s Rule serves as a basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Sincethe exo side will suffer from steric repulsion due to methyl groups so OH must add to the endo side in accordance with anti-Markovnikov’s Rule.

(c)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(c)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 12

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms.

Since the terminal olefinic carbon is less substituted OH must add to it in accordance with anti-Markovnikov’s Rule.

(d)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(d)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 16

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Sincehydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

(e)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 an alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(e)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 20

Anti-Markovnikov’s rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Since hydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

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Students have asked these similar questions

Identify the two diastereomeric hydroboration-oxidation products that can be formed from the following alkene by dragging the product pair to the product bin. Then suggest which product should be the major product or whether they will be formed in equal amounts by dragging the appropriate label to the bin under the products. Note: If one or more labels are incorrectly placed, a single red X will appear on the top left. 1) ВНз, ТHF 2) H-Ог. - ОН он Н Oн Н HI OH Н Он H ОН Н Он H Он Он. Н ОН Он ОН OH major praduct minor product minor product major product approximately equal amountsi

11.; (a) Similar to alkanes, hydrogen gas can undergo radical bromination according to the reaction below. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46 kcal·mole', for H-Br is 88 kcal'mole and for H-H is 104 kcal'mole'. hv H-H + Br-Br 2 H-Br (b) Calculate the overall AH for the above propagation steps (show all work).

As the molecular weight of alkenes increases, the boiling points also increase. Which ofthe following factors is best associated to this trend? *Dipole interactionGeometric isomerismStructural isomerismSurface areaA radical substitution reaction is primarily observed in the following reactions. Whichreaction is it? *Oxidation of but-2-eneChlorination of butaneBoiling of hex-3-eneCombustion of methaneWhich among the following compounds has the most electronegative carbon in itsstructure? *ButyneBenzeneBenzaldehydeCyclobutane

Answer 2

Question

Chapter 10.8, Problem 8E

(a)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves the sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(a)

Expert Solution

Explanation of Solution

The hydroboration-oxidation productis illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 4

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Since carbon 1 is less substituted thus OH must add to this carbon while H to other olefin carbon in accordance with anti-Markovnikov’s Rule.

(b)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(b)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 8

Anti-Markovnikov’s Rule serves as a basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Sincethe exo side will suffer from steric repulsion due to methyl groups so OH must add to the endo side in accordance with anti-Markovnikov’s Rule.

(c)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(c)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 12

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms.

Since the terminal olefinic carbon is less substituted OH must add to it in accordance with anti-Markovnikov’s Rule.

(d)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(d)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 16

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Sincehydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

(e)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 an alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(e)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 20

Anti-Markovnikov’s rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Since hydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 3

Question

Chapter 10.8, Problem 8E

(a)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves the sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(a)

Expert Solution

Explanation of Solution

The hydroboration-oxidation productis illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 4

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Since carbon 1 is less substituted thus OH must add to this carbon while H to other olefin carbon in accordance with anti-Markovnikov’s Rule.

(b)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(b)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 8

Anti-Markovnikov’s Rule serves as a basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Sincethe exo side will suffer from steric repulsion due to methyl groups so OH must add to the endo side in accordance with anti-Markovnikov’s Rule.

(c)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(c)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 12

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms.

Since the terminal olefinic carbon is less substituted OH must add to it in accordance with anti-Markovnikov’s Rule.

(d)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(d)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 16

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Sincehydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

(e)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 an alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(e)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 20

Anti-Markovnikov’s rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Since hydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Question

Chapter 10.8, Problem 8E

(a)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves the sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(a)

Expert Solution

Explanation of Solution

The hydroboration-oxidation productis illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 4

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Since carbon 1 is less substituted thus OH must add to this carbon while H to other olefin carbon in accordance with anti-Markovnikov’s Rule.

(b)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(b)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 8

Anti-Markovnikov’s Rule serves as a basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Sincethe exo side will suffer from steric repulsion due to methyl groups so OH must add to the endo side in accordance with anti-Markovnikov’s Rule.

(c)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(c)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 12

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms.

Since the terminal olefinic carbon is less substituted OH must add to it in accordance with anti-Markovnikov’s Rule.

(d)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(d)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 16

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Sincehydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

(e)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 an alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(e)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 20

Anti-Markovnikov’s rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Since hydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

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Answer 5

Chapter 10.8, Problem 8E

(a)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves the sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(a)

Expert Solution

Explanation of Solution

The hydroboration-oxidation productis illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 4

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Since carbon 1 is less substituted thus OH must add to this carbon while H to other olefin carbon in accordance with anti-Markovnikov’s Rule.

(b)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(b)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 8

Anti-Markovnikov’s Rule serves as a basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Sincethe exo side will suffer from steric repulsion due to methyl groups so OH must add to the endo side in accordance with anti-Markovnikov’s Rule.

(c)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(c)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 12

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms.

Since the terminal olefinic carbon is less substituted OH must add to it in accordance with anti-Markovnikov’s Rule.

(d)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(d)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 16

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Sincehydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

(e)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 an alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(e)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 20

Anti-Markovnikov’s rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Since hydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

Answer 6

Chapter 10.8, Problem 8E

(a)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves the sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(a)

Expert Solution

Explanation of Solution

The hydroboration-oxidation productis illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 4

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Since carbon 1 is less substituted thus OH must add to this carbon while H to other olefin carbon in accordance with anti-Markovnikov’s Rule.

Answer 7

Chapter 10.8, Problem 8E

(a)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves the sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

Answer 8

(a)

Expert Solution

Explanation of Solution

The hydroboration-oxidation productis illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 4

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Since carbon 1 is less substituted thus OH must add to this carbon while H to other olefin carbon in accordance with anti-Markovnikov’s Rule.

Answer 9

(a)

Expert Solution

Answer 10

(a)

Expert Solution

Answer 11

Expert Solution

Answer 12

(b)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(b)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 8

Anti-Markovnikov’s Rule serves as a basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Sincethe exo side will suffer from steric repulsion due to methyl groups so OH must add to the endo side in accordance with anti-Markovnikov’s Rule.

Answer 13

(b)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

Answer 14

(b)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 8

Anti-Markovnikov’s Rule serves as a basis of hydroboration. It states that the negative part of reagent must go to the carbon that has fewer alkyl substituents or more H atoms. Sincethe exo side will suffer from steric repulsion due to methyl groups so OH must add to the endo side in accordance with anti-Markovnikov’s Rule.

Answer 15

(b)

Expert Solution

Answer 16

(b)

Expert Solution

Answer 17

Expert Solution

Answer 18

(c)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(c)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 12

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms.

Since the terminal olefinic carbon is less substituted OH must add to it in accordance with anti-Markovnikov’s Rule.

Answer 19

(c)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

Answer 20

(c)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 12

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms.

Since the terminal olefinic carbon is less substituted OH must add to it in accordance with anti-Markovnikov’s Rule.

Answer 21

(c)

Expert Solution

Answer 22

(c)

Expert Solution

Answer 23

Expert Solution

Answer 24

(d)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(d)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 16

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Sincehydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

Answer 25

(d)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 and alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

Answer 26

(d)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 16

Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Sincehydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

Answer 27

(d)

Expert Solution

Answer 28

(d)

Expert Solution

Answer 29

Expert Solution

Answer 30

(e)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 an alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

(e)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 20

Anti-Markovnikov’s rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Since hydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

Answer 31

(e)

Interpretation Introduction

Interpretation: The structure of the major product formed from alkene indicated should be predicted.

Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from alkenes.

Hydroboration is essentially the addition of H− and BH2 across the alkene. For example, the reaction between BH3 an alkene to form syn-products illustrated as follows:

The mechanistic pathway can be illustrated as follows:

In the first step one equivalent of BH3 is added across the C−C π bond. This addition takes place such that boron approaches to less substituted carbon while the hydride ion adds to more substituted carbon. This occurs via a four-membered transition state that leads to syn-addition. So it is apt to refer this reaction as an addition that involves overall syn addition of BH3 .

Answer 32

(e)

Expert Solution

Explanation of Solution

The hydroboration-oxidation product is illustrated as below.

OWLv2 with LabSkills for Gilbert/Martin's Experimental Organic Chemistry: A Miniscale & Microscale Approach, 6th Edition, [Instant Access], 4 terms (24 months), Chapter 10.8, Problem 8E , additional homework tip 20

Anti-Markovnikov’s rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more H atoms. Since hydroboration reaction gives stereospecifically syn products so OH must add to carbon indicated in accordance with anti-Markovnikov’s Rule.

Answer 33

(e)

Expert Solution

Answer 34

(e)

Expert Solution

Answer 35

Expert Solution

Answer 36

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

Explanation of Solution

Explanation of Solution

Explanation of Solution

Explanation of Solution

Explanation of Solution

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