The detailed mechanism for the formation of the monoalkylborane in the given reaction is to be drawn. Also, the structure of trialkylborane that is ultimately produced is to be drawn. Concept introduction: Hydroboration is the addition of H and BH 2 groups across the carbon-carbon double bond in an alkene . These are stereospecific reactions in which the two said groups are added in a syn fashion. Hydroboration is also regioselective, where the hydrogen atom adds to the carbon atom with the greater number of alkyl groups (i.e., the most substituted carbon atom in the double bond), whereas the BH 2 group adds to the carbon atom with the fewer number of alkyl groups (i.e., the least substituted carbon atom in the double bond). Thus, the addition is said to occur according to anti-Markovnikov’s rule. As with the addition of BH 3 , each of these is a syn addition, and the bulkier B-containing portion adds preferentially to the less sterically hindered doubly bonded carbon atom. Once the trialkylborane is formed, it is then treated with a basic solution of hydrogen peroxide to convert it into an alcohol.

Question

Want to see the full answer?

Answer 1

Question

Chapter 12, Problem 12.21P

Interpretation Introduction

Interpretation:

The detailed mechanism for the formation of the monoalkylborane in the given reaction is to be drawn. Also, the structure of trialkylborane that is ultimately produced is to be drawn.

Concept introduction:

Hydroboration is the addition of H and BH2 groups across the carbon-carbon double bond in an alkene. These are stereospecific reactions in which the two said groups are added in a syn fashion. Hydroboration is also regioselective, where the hydrogen atom adds to the carbon atom with the greater number of alkyl groups (i.e., the most substituted carbon atom in the double bond), whereas the BH2 group adds to the carbon atom with the fewer number of alkyl groups (i.e., the least substituted carbon atom in the double bond). Thus, the addition is said to occur according to anti-Markovnikov’s rule.

As with the addition of BH3, each of these is a syn addition, and the bulkier B-containing portion adds preferentially to the less sterically hindered doubly bonded carbon atom. Once the trialkylborane is formed, it is then treated with a basic solution of hydrogen peroxide to convert it into an alcohol.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Don't used hand raiting

CS2(g) →CS(g) + S(g) The rate law is Rate = k[CS2] where k = 1.6 × 10−6 s−¹. S What is the concentration of CS2 after 5 hours if the initial concentration is 0.25 M?

CS2(g) → CS(g) + S(g) The rate law is Rate = k [CS2] where k = 1.6 × 10-6 s−1. S Calculate the half-life.

Answer 2

Question

Chapter 12, Problem 12.21P

Interpretation Introduction

Interpretation:

The detailed mechanism for the formation of the monoalkylborane in the given reaction is to be drawn. Also, the structure of trialkylborane that is ultimately produced is to be drawn.

Concept introduction:

Hydroboration is the addition of H and BH2 groups across the carbon-carbon double bond in an alkene. These are stereospecific reactions in which the two said groups are added in a syn fashion. Hydroboration is also regioselective, where the hydrogen atom adds to the carbon atom with the greater number of alkyl groups (i.e., the most substituted carbon atom in the double bond), whereas the BH2 group adds to the carbon atom with the fewer number of alkyl groups (i.e., the least substituted carbon atom in the double bond). Thus, the addition is said to occur according to anti-Markovnikov’s rule.

As with the addition of BH3, each of these is a syn addition, and the bulkier B-containing portion adds preferentially to the less sterically hindered doubly bonded carbon atom. Once the trialkylborane is formed, it is then treated with a basic solution of hydrogen peroxide to convert it into an alcohol.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 12, Problem 12.21P

Interpretation Introduction

Interpretation:

The detailed mechanism for the formation of the monoalkylborane in the given reaction is to be drawn. Also, the structure of trialkylborane that is ultimately produced is to be drawn.

Concept introduction:

Hydroboration is the addition of H and BH2 groups across the carbon-carbon double bond in an alkene. These are stereospecific reactions in which the two said groups are added in a syn fashion. Hydroboration is also regioselective, where the hydrogen atom adds to the carbon atom with the greater number of alkyl groups (i.e., the most substituted carbon atom in the double bond), whereas the BH2 group adds to the carbon atom with the fewer number of alkyl groups (i.e., the least substituted carbon atom in the double bond). Thus, the addition is said to occur according to anti-Markovnikov’s rule.

As with the addition of BH3, each of these is a syn addition, and the bulkier B-containing portion adds preferentially to the less sterically hindered doubly bonded carbon atom. Once the trialkylborane is formed, it is then treated with a basic solution of hydrogen peroxide to convert it into an alcohol.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 12, Problem 12.21P

Interpretation Introduction

Interpretation:

The detailed mechanism for the formation of the monoalkylborane in the given reaction is to be drawn. Also, the structure of trialkylborane that is ultimately produced is to be drawn.

Concept introduction:

Hydroboration is the addition of H and BH2 groups across the carbon-carbon double bond in an alkene. These are stereospecific reactions in which the two said groups are added in a syn fashion. Hydroboration is also regioselective, where the hydrogen atom adds to the carbon atom with the greater number of alkyl groups (i.e., the most substituted carbon atom in the double bond), whereas the BH2 group adds to the carbon atom with the fewer number of alkyl groups (i.e., the least substituted carbon atom in the double bond). Thus, the addition is said to occur according to anti-Markovnikov’s rule.

As with the addition of BH3, each of these is a syn addition, and the bulkier B-containing portion adds preferentially to the less sterically hindered doubly bonded carbon atom. Once the trialkylborane is formed, it is then treated with a basic solution of hydrogen peroxide to convert it into an alcohol.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 12, Problem 12.21P

Interpretation Introduction

Interpretation:

The detailed mechanism for the formation of the monoalkylborane in the given reaction is to be drawn. Also, the structure of trialkylborane that is ultimately produced is to be drawn.

Concept introduction:

Hydroboration is the addition of H and BH2 groups across the carbon-carbon double bond in an alkene. These are stereospecific reactions in which the two said groups are added in a syn fashion. Hydroboration is also regioselective, where the hydrogen atom adds to the carbon atom with the greater number of alkyl groups (i.e., the most substituted carbon atom in the double bond), whereas the BH2 group adds to the carbon atom with the fewer number of alkyl groups (i.e., the least substituted carbon atom in the double bond). Thus, the addition is said to occur according to anti-Markovnikov’s rule.

As with the addition of BH3, each of these is a syn addition, and the bulkier B-containing portion adds preferentially to the less sterically hindered doubly bonded carbon atom. Once the trialkylborane is formed, it is then treated with a basic solution of hydrogen peroxide to convert it into an alcohol.

Answer 6

Chapter 12, Problem 12.21P

Interpretation Introduction

Interpretation:

The detailed mechanism for the formation of the monoalkylborane in the given reaction is to be drawn. Also, the structure of trialkylborane that is ultimately produced is to be drawn.

Concept introduction:

Hydroboration is the addition of H and BH2 groups across the carbon-carbon double bond in an alkene. These are stereospecific reactions in which the two said groups are added in a syn fashion. Hydroboration is also regioselective, where the hydrogen atom adds to the carbon atom with the greater number of alkyl groups (i.e., the most substituted carbon atom in the double bond), whereas the BH2 group adds to the carbon atom with the fewer number of alkyl groups (i.e., the least substituted carbon atom in the double bond). Thus, the addition is said to occur according to anti-Markovnikov’s rule.

As with the addition of BH3, each of these is a syn addition, and the bulkier B-containing portion adds preferentially to the less sterically hindered doubly bonded carbon atom. Once the trialkylborane is formed, it is then treated with a basic solution of hydrogen peroxide to convert it into an alcohol.

Answer 7

Chapter 12, Problem 12.21P

Interpretation Introduction

Interpretation:

The detailed mechanism for the formation of the monoalkylborane in the given reaction is to be drawn. Also, the structure of trialkylborane that is ultimately produced is to be drawn.

Concept introduction:

Hydroboration is the addition of H and BH2 groups across the carbon-carbon double bond in an alkene. These are stereospecific reactions in which the two said groups are added in a syn fashion. Hydroboration is also regioselective, where the hydrogen atom adds to the carbon atom with the greater number of alkyl groups (i.e., the most substituted carbon atom in the double bond), whereas the BH2 group adds to the carbon atom with the fewer number of alkyl groups (i.e., the least substituted carbon atom in the double bond). Thus, the addition is said to occur according to anti-Markovnikov’s rule.

As with the addition of BH3, each of these is a syn addition, and the bulkier B-containing portion adds preferentially to the less sterically hindered doubly bonded carbon atom. Once the trialkylborane is formed, it is then treated with a basic solution of hydrogen peroxide to convert it into an alcohol.

Answer 8

Expert Solution & Answer

Answer 9

Expert Solution & Answer

Answer 10

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 11

Ch. 12 - Prob. 12.1P Ch. 12 - Prob. 12.2P Ch. 12 - Prob. 12.3P Ch. 12 - Prob. 12.4P Ch. 12 - Prob. 12.5P Ch. 12 - Prob. 12.6P Ch. 12 - Prob. 12.7P Ch. 12 - Prob. 12.8P Ch. 12 - Prob. 12.9P Ch. 12 - Prob. 12.10P

Solution Summary: The author explains the structure of trialkylborane that is ultimately produced. Hydroboration is a syn addition, whereas the bulkier B-containing portion adds preferentially to the less sterically hindere

Concept explainers

Videos

Want to see the full answer?

Chapter 12 Solutions