Two different ways of synthesizing the given compound via carbene addition by using a different alkene are to be provided. Concept introduction: A carbene is a species containing a carbon atom that has two bonds and a lone pair of electrons. Carbenes are typically highly electrophilic due to the lack of an octet and are sp 2 hybridized. The lone pair of electrons occupies a hybrid orbital, leaving the p orbital empty. Thus, carbenes resemble a carbocation and are generally highly electron-deficient. Chloroform is a precursor to generate a carbene. When an alkyl trihalide is treated with a strong base in the presence of cyclohexane, a dihalocarbene is generated in two steps via α - elimination. The base first deprotonates the alkyl trihalide, which is weakly acidic. In step two, the halogen atom departs to generate a carbene. In an electrophilic addition reaction, alkenes react with carbenes, forming a three-membered ring. The reaction consist of addition of the alkene to an electrophilic carbene. The lone pair can donate back so that a carbocation does not actually form in same step. The stereochemistry of the substituents in the alkene is conserved in the product.

Question

Want to see the full answer?

Answer 1

Question

Chapter 12, Problem 12.4P

Interpretation Introduction

Interpretation:

Two different ways of synthesizing the given compound via carbene addition by using a different alkene are to be provided.

Concept introduction:

A carbene is a species containing a carbon atom that has two bonds and a lone pair of electrons. Carbenes are typically highly electrophilic due to the lack of an octet and are sp2 hybridized. The lone pair of electrons occupies a hybrid orbital, leaving the p orbital empty. Thus, carbenes resemble a carbocation and are generally highly electron-deficient.

Chloroform is a precursor to generate a carbene. When an alkyl trihalide is treated with a strong base in the presence of cyclohexane, a dihalocarbene is generated in two steps via α- elimination. The base first deprotonates the alkyl trihalide, which is weakly acidic. In step two, the halogen atom departs to generate a carbene.

In an electrophilic addition reaction, alkenes react with carbenes, forming a three-membered ring. The reaction consist of addition of the alkene to an electrophilic carbene. The lone pair can donate back so that a carbocation does not actually form in same step. The stereochemistry of the substituents in the alkene is conserved in the product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Organic Chemistry Problem. Please help with figuring out what steps to take to obtain the product of the reaction shown. Thank you

Please help with Organic Chemistry problem. What is the product of reaction shown? (what should be where the question mark is ?) Thank you

Problem: Show how the following compound can be produced from an alkene. Include the alkene, the reagents, and any special reaction conditions. Pay attention to stereochemistry.

Answer 2

Question

Chapter 12, Problem 12.4P

Interpretation Introduction

Interpretation:

Two different ways of synthesizing the given compound via carbene addition by using a different alkene are to be provided.

Concept introduction:

A carbene is a species containing a carbon atom that has two bonds and a lone pair of electrons. Carbenes are typically highly electrophilic due to the lack of an octet and are sp2 hybridized. The lone pair of electrons occupies a hybrid orbital, leaving the p orbital empty. Thus, carbenes resemble a carbocation and are generally highly electron-deficient.

Chloroform is a precursor to generate a carbene. When an alkyl trihalide is treated with a strong base in the presence of cyclohexane, a dihalocarbene is generated in two steps via α- elimination. The base first deprotonates the alkyl trihalide, which is weakly acidic. In step two, the halogen atom departs to generate a carbene.

In an electrophilic addition reaction, alkenes react with carbenes, forming a three-membered ring. The reaction consist of addition of the alkene to an electrophilic carbene. The lone pair can donate back so that a carbocation does not actually form in same step. The stereochemistry of the substituents in the alkene is conserved in the product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 12, Problem 12.4P

Interpretation Introduction

Interpretation:

Two different ways of synthesizing the given compound via carbene addition by using a different alkene are to be provided.

Concept introduction:

A carbene is a species containing a carbon atom that has two bonds and a lone pair of electrons. Carbenes are typically highly electrophilic due to the lack of an octet and are sp2 hybridized. The lone pair of electrons occupies a hybrid orbital, leaving the p orbital empty. Thus, carbenes resemble a carbocation and are generally highly electron-deficient.

Chloroform is a precursor to generate a carbene. When an alkyl trihalide is treated with a strong base in the presence of cyclohexane, a dihalocarbene is generated in two steps via α- elimination. The base first deprotonates the alkyl trihalide, which is weakly acidic. In step two, the halogen atom departs to generate a carbene.

In an electrophilic addition reaction, alkenes react with carbenes, forming a three-membered ring. The reaction consist of addition of the alkene to an electrophilic carbene. The lone pair can donate back so that a carbocation does not actually form in same step. The stereochemistry of the substituents in the alkene is conserved in the product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 12, Problem 12.4P

Interpretation Introduction

Interpretation:

Two different ways of synthesizing the given compound via carbene addition by using a different alkene are to be provided.

Concept introduction:

A carbene is a species containing a carbon atom that has two bonds and a lone pair of electrons. Carbenes are typically highly electrophilic due to the lack of an octet and are sp2 hybridized. The lone pair of electrons occupies a hybrid orbital, leaving the p orbital empty. Thus, carbenes resemble a carbocation and are generally highly electron-deficient.

Chloroform is a precursor to generate a carbene. When an alkyl trihalide is treated with a strong base in the presence of cyclohexane, a dihalocarbene is generated in two steps via α- elimination. The base first deprotonates the alkyl trihalide, which is weakly acidic. In step two, the halogen atom departs to generate a carbene.

In an electrophilic addition reaction, alkenes react with carbenes, forming a three-membered ring. The reaction consist of addition of the alkene to an electrophilic carbene. The lone pair can donate back so that a carbocation does not actually form in same step. The stereochemistry of the substituents in the alkene is conserved in the product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 12, Problem 12.4P

Interpretation Introduction

Interpretation:

Two different ways of synthesizing the given compound via carbene addition by using a different alkene are to be provided.

Concept introduction:

A carbene is a species containing a carbon atom that has two bonds and a lone pair of electrons. Carbenes are typically highly electrophilic due to the lack of an octet and are sp2 hybridized. The lone pair of electrons occupies a hybrid orbital, leaving the p orbital empty. Thus, carbenes resemble a carbocation and are generally highly electron-deficient.

Chloroform is a precursor to generate a carbene. When an alkyl trihalide is treated with a strong base in the presence of cyclohexane, a dihalocarbene is generated in two steps via α- elimination. The base first deprotonates the alkyl trihalide, which is weakly acidic. In step two, the halogen atom departs to generate a carbene.

In an electrophilic addition reaction, alkenes react with carbenes, forming a three-membered ring. The reaction consist of addition of the alkene to an electrophilic carbene. The lone pair can donate back so that a carbocation does not actually form in same step. The stereochemistry of the substituents in the alkene is conserved in the product.

Answer 6

Chapter 12, Problem 12.4P

Interpretation Introduction

Interpretation:

Two different ways of synthesizing the given compound via carbene addition by using a different alkene are to be provided.

Concept introduction:

A carbene is a species containing a carbon atom that has two bonds and a lone pair of electrons. Carbenes are typically highly electrophilic due to the lack of an octet and are sp2 hybridized. The lone pair of electrons occupies a hybrid orbital, leaving the p orbital empty. Thus, carbenes resemble a carbocation and are generally highly electron-deficient.

Chloroform is a precursor to generate a carbene. When an alkyl trihalide is treated with a strong base in the presence of cyclohexane, a dihalocarbene is generated in two steps via α- elimination. The base first deprotonates the alkyl trihalide, which is weakly acidic. In step two, the halogen atom departs to generate a carbene.

In an electrophilic addition reaction, alkenes react with carbenes, forming a three-membered ring. The reaction consist of addition of the alkene to an electrophilic carbene. The lone pair can donate back so that a carbocation does not actually form in same step. The stereochemistry of the substituents in the alkene is conserved in the product.

Answer 7

Chapter 12, Problem 12.4P

Interpretation Introduction

Interpretation:

Two different ways of synthesizing the given compound via carbene addition by using a different alkene are to be provided.

Concept introduction:

A carbene is a species containing a carbon atom that has two bonds and a lone pair of electrons. Carbenes are typically highly electrophilic due to the lack of an octet and are sp2 hybridized. The lone pair of electrons occupies a hybrid orbital, leaving the p orbital empty. Thus, carbenes resemble a carbocation and are generally highly electron-deficient.

Chloroform is a precursor to generate a carbene. When an alkyl trihalide is treated with a strong base in the presence of cyclohexane, a dihalocarbene is generated in two steps via α- elimination. The base first deprotonates the alkyl trihalide, which is weakly acidic. In step two, the halogen atom departs to generate a carbene.

In an electrophilic addition reaction, alkenes react with carbenes, forming a three-membered ring. The reaction consist of addition of the alkene to an electrophilic carbene. The lone pair can donate back so that a carbocation does not actually form in same step. The stereochemistry of the substituents in the alkene is conserved in the product.

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 describes two different ways of synthesizing the given compound via carbene addition by using a different alkene.

Concept explainers

Videos

Want to see the full answer?

Chapter 12 Solutions