A mechanism for the unexpected formation of an isomer of laurene instead of laurene in the Wittig reaction shown is to be proposed. Concept introduction: Wittig reagents can act as bases and bring about enolization of ketones. The enolate ion, if optically active, can yield two diastereomers during isomerization. The more stable diastereomer will take part in a Wittig reaction. To propose A mechanism for the unexpected formation of an isomer of laurene instead of laurene in the Wittig reaction shown.

Question

Want to see the full answer?

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.SE, Problem 33MP

Interpretation Introduction

Interpretation:

A mechanism for the unexpected formation of an isomer of laurene instead of laurene in the Wittig reaction shown is to be proposed.

Concept introduction:

Wittig reagents can act as bases and bring about enolization of ketones. The enolate ion, if optically active, can yield two diastereomers during isomerization. The more stable diastereomer will take part in a Wittig reaction.

To propose

A mechanism for the unexpected formation of an isomer of laurene instead of laurene in the Wittig reaction shown.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

If phenoxide ion is allowed to react with 1-bromopentane, pentyl phenyl ether is obtained. However, if cyclohexane is used as the alkyl halide, the major products are phenol and cyclohexene. Explain how these products were formed.

A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring, but in this case it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction.

2,3-Dimethylbutane reacts with bromine in the presence of light to give a mono brominated product. The further reaction gives a good yield of a dibrominated product. Predict the structures of these products, and propose a mechanism for the formation of the mono brominated product.

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.SE, Problem 33MP

Interpretation Introduction

Interpretation:

A mechanism for the unexpected formation of an isomer of laurene instead of laurene in the Wittig reaction shown is to be proposed.

Concept introduction:

Wittig reagents can act as bases and bring about enolization of ketones. The enolate ion, if optically active, can yield two diastereomers during isomerization. The more stable diastereomer will take part in a Wittig reaction.

To propose

A mechanism for the unexpected formation of an isomer of laurene instead of laurene in the Wittig reaction shown.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.SE, Problem 33MP

Interpretation Introduction

Interpretation:

A mechanism for the unexpected formation of an isomer of laurene instead of laurene in the Wittig reaction shown is to be proposed.

Concept introduction:

Wittig reagents can act as bases and bring about enolization of ketones. The enolate ion, if optically active, can yield two diastereomers during isomerization. The more stable diastereomer will take part in a Wittig reaction.

To propose

A mechanism for the unexpected formation of an isomer of laurene instead of laurene in the Wittig reaction shown.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.SE, Problem 33MP

Interpretation Introduction