The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn. Concept introduction: The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

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Answer 1

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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 18.71P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn.

Concept introduction:

The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

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In a Wittig reaction, a ketone or aldehyde reacts as an electrophile with a nucleophile called a Wittig reagent (or phosphonium ylide) to produce an alkene. The Wittig reagent is commonly synthesized first in a two-step process beginning with an alkyl halide, then reacted with the carbonyl compound. In this problem, you'll explore the mechanism of a multi-step synthesis to make an alkene using the Wittig approach.

Draw a detailed mechanism of the following reactions and determine the major product:

Draw a complete detailed mechanism for this reaction.

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 18.71P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn.

Concept introduction:

The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

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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 18, Problem 18.71P

Interpretation Introduction

Interpretation:

The detailed mechanism for the given reaction of benzaldehyde with propenenitrile in presence of a catalytic amount of NaCN is to be drawn.

Concept introduction:

The aromatic aldehyde can be converted to a good nucleophile as carbanion by reacting it with catalytic cyanide ion. The carbanion undergoes nucleophilic addition reaction with polar π bond or conjugated polar π bond like conjugated nitrile. In the first step, the cyanide ion undergoes nucleophilic addition with aromatic aldehyde and forms a cyanohydrin. The cyanohydrin in presence of base like hydroxide ion forms a resonance stabilized carbanion, which further adds to conjugated nitrile and forms an intermediate by proton transfer. The intermediate formed then undergoes elimination of cyanide forming carbonyl derivative having cyanide functional group.

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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 18, Problem 18.71P

Interpretation Introduction