The explanation to why phosphonium ylide reacts with aldehyde or ketone to form an alkene but a sulfonium ylide forms an epoxide has to be given. Concept introduction: Ylides: Ylides are those compounds in which a negatively charged species such as carbanion is attached directly to a heteroatom like sulfur and phosphorous. Some examples of such compounds are phosphorus ylides, sulfonium ylides, carbonyl ylides and oxonium ylides.

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 16, Problem 82P

Interpretation Introduction

Interpretation:

The explanation to why phosphonium ylide reacts with aldehyde or ketone to form an alkene but a sulfonium ylide forms an epoxide has to be given.

Concept introduction:

Ylides:

Ylides are those compounds in which a negatively charged species such as carbanion is attached directly to a heteroatom like sulfur and phosphorous. Some examples of such compounds are phosphorus ylides, sulfonium ylides, carbonyl ylides and oxonium ylides.

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Unlike a phosphonium ylide that reacts with an aldehyde or a ketone to form an alkene, a sulfonium ylide reacts with an aldehyde or a ketone to form anepoxide. Explain why one ylide forms an alkene, whereas the other forms an epoxide.

Explain using resonance structures of the intermediates (please explain and draw them out) why the bromination of phenol is faster than the bromination of phenyl ester?

Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide. Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.

Answer 2

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 16, Problem 82P

Interpretation Introduction

Interpretation:

The explanation to why phosphonium ylide reacts with aldehyde or ketone to form an alkene but a sulfonium ylide forms an epoxide has to be given.

Concept introduction:

Ylides:

Ylides are those compounds in which a negatively charged species such as carbanion is attached directly to a heteroatom like sulfur and phosphorous. Some examples of such compounds are phosphorus ylides, sulfonium ylides, carbonyl ylides and oxonium ylides.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 16, Problem 82P

Interpretation Introduction

Interpretation:

The explanation to why phosphonium ylide reacts with aldehyde or ketone to form an alkene but a sulfonium ylide forms an epoxide has to be given.

Concept introduction:

Ylides:

Ylides are those compounds in which a negatively charged species such as carbanion is attached directly to a heteroatom like sulfur and phosphorous. Some examples of such compounds are phosphorus ylides, sulfonium ylides, carbonyl ylides and oxonium ylides.

Expert Solution & Answer

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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 aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 16, Problem 82P

Interpretation Introduction