The complete, detailed mechanism for the given reaction is to be drawn, and major product for the same reaction is to be predicted. Concept introduction: The intramolecular Claisen condensation of the diester, on treatment with a strong base, leads to form the β-keto ester. This is known as the Dieckmann condensation reaction. the α carbon of the carbonyl compound has an acidic proton, which can be easily abstracted by the strong base. The carbanion is formed, which is resonance stabilized with corresponding more stable enolate form. This enolate adds the second carbonyl carbon of the diester, and simultaneously, the alkoxide group ( RO - ) is eliminated to form the β-keto ester as the product. So the Dieckmann condensation involves intramolecular nucleophilic addition-elimination reaction. In most of the cyclization reaction, Dieckmann condensation occurs. Dieckmann condensation does not occur when the ring size is less than five-member or more than eight members due to angle strain. The proton of α carbon of the ketones and aldehydes is more acidic than that of ester.

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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 21, Problem 21.28P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and major product for the same reaction is to be predicted.

Concept introduction:

The intramolecular Claisen condensation of the diester, on treatment with a strong base, leads to form the β-keto ester. This is known as the Dieckmann condensation reaction. the α carbon of the carbonyl compound has an acidic proton, which can be easily abstracted by the strong base. The carbanion is formed, which is resonance stabilized with corresponding more stable enolate form. This enolate adds the second carbonyl carbon of the diester, and simultaneously, the alkoxide group (RO-) is eliminated to form the β-keto ester as the product. So the Dieckmann condensation involves intramolecular nucleophilic addition-elimination reaction. In most of the cyclization reaction, Dieckmann condensation occurs. Dieckmann condensation does not occur when the ring size is less than five-member or more than eight members due to angle strain. The proton of α carbon of the ketones and aldehydes is more acidic than that of ester.

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81. a. Propose a mechanism for the following reaction: OH CH2=CHCHC=N b. What is the product of the following reaction? HO H₂O N=CCH2CH2CH OH HO CH3CCH=CH2 H₂O C=N 82. Unlike a phosphonium ylide that reacts with an aldehyde or a ketone to form an alkene a sulfonium ulia

For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.

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 21, Problem 21.28P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and major product for the same reaction is to be predicted.

Concept introduction:

The intramolecular Claisen condensation of the diester, on treatment with a strong base, leads to form the β-keto ester. This is known as the Dieckmann condensation reaction. the α carbon of the carbonyl compound has an acidic proton, which can be easily abstracted by the strong base. The carbanion is formed, which is resonance stabilized with corresponding more stable enolate form. This enolate adds the second carbonyl carbon of the diester, and simultaneously, the alkoxide group (RO-) is eliminated to form the β-keto ester as the product. So the Dieckmann condensation involves intramolecular nucleophilic addition-elimination reaction. In most of the cyclization reaction, Dieckmann condensation occurs. Dieckmann condensation does not occur when the ring size is less than five-member or more than eight members due to angle strain. The proton of α carbon of the ketones and aldehydes is more acidic than that of ester.

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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 21, Problem 21.28P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and major product for the same reaction is to be predicted.

Concept introduction:

The intramolecular Claisen condensation of the diester, on treatment with a strong base, leads to form the β-keto ester. This is known as the Dieckmann condensation reaction. the α carbon of the carbonyl compound has an acidic proton, which can be easily abstracted by the strong base. The carbanion is formed, which is resonance stabilized with corresponding more stable enolate form. This enolate adds the second carbonyl carbon of the diester, and simultaneously, the alkoxide group (RO-) is eliminated to form the β-keto ester as the product. So the Dieckmann condensation involves intramolecular nucleophilic addition-elimination reaction. In most of the cyclization reaction, Dieckmann condensation occurs. Dieckmann condensation does not occur when the ring size is less than five-member or more than eight members due to angle strain. The proton of α carbon of the ketones and aldehydes is more acidic than that of ester.

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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 21, Problem 21.28P

Interpretation Introduction