A plausible mechanism for the formation of the compound 2 from the compound 1 has to be provided. Concept Introduction : The Pictet-Spengler condensation reaction is also known as Pictet-Spengler tetrahydroisoquinoline synthesis. It is an organic reaction used to convert a β-arylethylamine and an aldehyde or ketone to a tetrahydroisoquinoline using an acid catalyst. The mechanism begins with protonation of the carbonyl oxygen by the acid which is subsequently attacked by the amine reagent. Proton transfer steps and the release of a water molecule result in the formation of a protonated imine intermediate, which then undergoes a 6-endo-trig cyclization reaction with loss of aromaticity of the aryl ring. A final deprotonation step restores the aromaticity and results in tetrahydroisoquinoline product. To find: Provide a plausible mechanism for the formation of the compound 2 from the compound 1 Generate the intermediate 3

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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 22, Problem 98CP

Interpretation Introduction

Interpretation: A plausible mechanism for the formation of the compound 2 from the compound 1 has to be provided.

Concept Introduction:

The Pictet-Spengler condensation reaction is also known as Pictet-Spengler tetrahydroisoquinoline synthesis. It is an organic reaction used to convert a β-arylethylamine and an aldehyde or ketone to a tetrahydroisoquinoline using an acid catalyst. The mechanism begins with protonation of the carbonyl oxygen by the acid which is subsequently attacked by the amine reagent. Proton transfer steps and the release of a water molecule result in the formation of a protonated imine intermediate, which then undergoes a 6-endo-trig cyclization reaction with loss of aromaticity of the aryl ring. A final deprotonation step restores the aromaticity and results in tetrahydroisoquinoline product.

To find: Provide a plausible mechanism for the formation of the compound 2 from the compound 1

Generate the intermediate 3

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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 22, Problem 98CP

Interpretation Introduction

Interpretation: A plausible mechanism for the formation of the compound 2 from the compound 1 has to be provided.

Concept Introduction:

The Pictet-Spengler condensation reaction is also known as Pictet-Spengler tetrahydroisoquinoline synthesis. It is an organic reaction used to convert a β-arylethylamine and an aldehyde or ketone to a tetrahydroisoquinoline using an acid catalyst. The mechanism begins with protonation of the carbonyl oxygen by the acid which is subsequently attacked by the amine reagent. Proton transfer steps and the release of a water molecule result in the formation of a protonated imine intermediate, which then undergoes a 6-endo-trig cyclization reaction with loss of aromaticity of the aryl ring. A final deprotonation step restores the aromaticity and results in tetrahydroisoquinoline product.

To find: Provide a plausible mechanism for the formation of the compound 2 from the compound 1

Generate the intermediate 3

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Check out a sample textbook solution

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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 22, Problem 98CP

Interpretation Introduction

Interpretation: A plausible mechanism for the formation of the compound 2 from the compound 1 has to be provided.

Concept Introduction:

The Pictet-Spengler condensation reaction is also known as Pictet-Spengler tetrahydroisoquinoline synthesis. It is an organic reaction used to convert a β-arylethylamine and an aldehyde or ketone to a tetrahydroisoquinoline using an acid catalyst. The mechanism begins with protonation of the carbonyl oxygen by the acid which is subsequently attacked by the amine reagent. Proton transfer steps and the release of a water molecule result in the formation of a protonated imine intermediate, which then undergoes a 6-endo-trig cyclization reaction with loss of aromaticity of the aryl ring. A final deprotonation step restores the aromaticity and results in tetrahydroisoquinoline product.

To find: Provide a plausible mechanism for the formation of the compound 2 from the compound 1

Generate the intermediate 3

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 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 22, Problem 98CP

Interpretation Introduction