The detailed mechanism for the given reaction of benzaldehyde with a catalytic amount of KCN is to be drawn. Concept introduction: The benzoin condensation involves the addition of two aromatic aldehydes and produces acyloin. The reaction is catalyzed by cyanide ion which acts as a nucleophile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrine. The cyanohydrin, in presence of base like hydroxide ion, forms a resonance stabilized carbanion, which further adds to the second aromatic aldehyde and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide to produce a corresponding acyloin product ( α- hydroxy ketone ).

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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 18, Problem 18.70P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with a catalytic amount of KCN is to be drawn.

Concept introduction:

The benzoin condensation involves the addition of two aromatic aldehydes and produces acyloin. The reaction is catalyzed by cyanide ion which acts as a nucleophile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrine. The cyanohydrin, in presence of base like hydroxide ion, forms a resonance stabilized carbanion, which further adds to the second aromatic aldehyde and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide to produce a corresponding acyloin product (α- hydroxy ketone).

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If a reaction occurs, what would be the major products? Please include a detailed explanation as well as a drawing showing how the reaction occurs and what the final product is.

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 18, Problem 18.70P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with a catalytic amount of KCN is to be drawn.

Concept introduction:

The benzoin condensation involves the addition of two aromatic aldehydes and produces acyloin. The reaction is catalyzed by cyanide ion which acts as a nucleophile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrine. The cyanohydrin, in presence of base like hydroxide ion, forms a resonance stabilized carbanion, which further adds to the second aromatic aldehyde and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide to produce a corresponding acyloin product (α- hydroxy ketone).

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Answer 3

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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 18, Problem 18.70P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with a catalytic amount of KCN is to be drawn.

Concept introduction:

The benzoin condensation involves the addition of two aromatic aldehydes and produces acyloin. The reaction is catalyzed by cyanide ion which acts as a nucleophile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrine. The cyanohydrin, in presence of base like hydroxide ion, forms a resonance stabilized carbanion, which further adds to the second aromatic aldehyde and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide to produce a corresponding acyloin product (α- hydroxy ketone).

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Answer 4

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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 18, Problem 18.70P

Interpretation Introduction