The total synthesis of the anticholinergic drug, the structure formulas for the intermediates has to be proposed. Concept introduction: Michael reaction: In 1, 4 addition the Nucleophile is added to the carbon β to the carbonyl while the hydrogen is added to the carbon α to the carbonyl. Dieckann Condensation The base-catalyzed intramolecular condensation of a diester. The Dieckmann Condensation works well to produce 5- or 6-membered cyclic β -keto esters, and is usually affected with sodium alkoxide in alcoholic solvent. Sodium borohydride is reducing agent, generally aldehyde and ketone reduced to alcohol.

Question

Propose a synthesis pathway for the production of the following compounds (d) to (e) from the given starting materials plus necessary organic and inorganic reagents.

Answer 1

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 19, Problem 19.49P

Interpretation Introduction

Interpretation:

The total synthesis of the anticholinergic drug, the structure formulas for the intermediates has to be proposed.

Concept introduction:

Michael reaction:

In 1, 4 addition the Nucleophile is added to the carbon β to the carbonyl while the hydrogen is added to the carbon α to the carbonyl.

Dieckann Condensation

The base-catalyzed intramolecular condensation of a diester. The Dieckmann Condensation works well to produce 5- or 6-membered cyclic β-keto esters, and is usually affected with sodium alkoxide in alcoholic solvent.

Sodium borohydride is reducing agent, generally aldehyde and ketone reduced to alcohol.

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Propose a synthesis pathway for the production of the following compounds (d) to (e) from the given starting materials plus necessary organic and inorganic reagents.

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Answer 2

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 19, Problem 19.49P

Interpretation Introduction

Interpretation:

The total synthesis of the anticholinergic drug, the structure formulas for the intermediates has to be proposed.

Concept introduction:

Michael reaction:

In 1, 4 addition the Nucleophile is added to the carbon β to the carbonyl while the hydrogen is added to the carbon α to the carbonyl.

Dieckann Condensation

The base-catalyzed intramolecular condensation of a diester. The Dieckmann Condensation works well to produce 5- or 6-membered cyclic β-keto esters, and is usually affected with sodium alkoxide in alcoholic solvent.

Sodium borohydride is reducing agent, generally aldehyde and ketone reduced to alcohol.

Expert Solution & Answer

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Check out sample textbook solution

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 19, Problem 19.49P

Interpretation Introduction

Interpretation:

The total synthesis of the anticholinergic drug, the structure formulas for the intermediates has to be proposed.

Concept introduction:

Michael reaction:

In 1, 4 addition the Nucleophile is added to the carbon β to the carbonyl while the hydrogen is added to the carbon α to the carbonyl.

Dieckann Condensation

The base-catalyzed intramolecular condensation of a diester. The Dieckmann Condensation works well to produce 5- or 6-membered cyclic β-keto esters, and is usually affected with sodium alkoxide in alcoholic solvent.

Sodium borohydride is reducing agent, generally aldehyde and ketone reduced to alcohol.

Expert Solution & Answer

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See solution

Check out sample textbook 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 19, Problem 19.49P

Interpretation Introduction