To predict both products of Dieckmann cyclization when the given compound is treated with sodium ethoxide. Concept introduction: Dieckmann cyclization is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound within the same molecule in presence of a strong base to form a cyclic β -keto ester or a cyclic β -diketone, respectively. Deprotonation of α carbon to form ester enolate Attach of enolate ion with the carbonyl of ester or ketone ( nucleophilic attack ) Loss of alkoxide ion to reform carbonyl Acidic workup If the claisen condensation reaction takes place within the same molecule means a ring is formed. This is known as intramolecular claisen condensation ( Dieckmann cyclization ) Please note the base considered for the reaction should have the same alkoxide group which is present in the ester of the starting material to avoid transesterification.

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Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21.4, Problem 28CC

Interpretation Introduction

Interpretation:

To predict both products of Dieckmann cyclization when the given compound is treated with sodium ethoxide.

Concept introduction:

Dieckmann cyclization is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound within the same molecule in presence of a strong base to form a cyclic $β$ -keto ester or a cyclic $β$ -diketone, respectively.

Deprotonation of $α$ carbon to form ester enolate

Attach of enolate ion with the carbonyl of ester or ketone (nucleophilic attack)

Loss of alkoxide ion to reform carbonyl

Acidic workup

If the claisen condensation reaction takes place within the same molecule means a ring is formed. This is known as intramolecular claisen condensation (Dieckmann cyclization)

Please note the base considered for the reaction should have the same alkoxide group which is present in the ester of the starting material to avoid transesterification.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21.4, Problem 28CC

Interpretation Introduction

Interpretation:

To predict both products of Dieckmann cyclization when the given compound is treated with sodium ethoxide.

Concept introduction:

Dieckmann cyclization is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound within the same molecule in presence of a strong base to form a cyclic $β$ -keto ester or a cyclic $β$ -diketone, respectively.

Deprotonation of $α$ carbon to form ester enolate

Attach of enolate ion with the carbonyl of ester or ketone (nucleophilic attack)

Loss of alkoxide ion to reform carbonyl

Acidic workup

If the claisen condensation reaction takes place within the same molecule means a ring is formed. This is known as intramolecular claisen condensation (Dieckmann cyclization)

Please note the base considered for the reaction should have the same alkoxide group which is present in the ester of the starting material to avoid transesterification.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21.4, Problem 28CC

Interpretation Introduction

Interpretation:

To predict both products of Dieckmann cyclization when the given compound is treated with sodium ethoxide.

Concept introduction:

Dieckmann cyclization is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound within the same molecule in presence of a strong base to form a cyclic $β$ -keto ester or a cyclic $β$ -diketone, respectively.

Deprotonation of $α$ carbon to form ester enolate

Attach of enolate ion with the carbonyl of ester or ketone (nucleophilic attack)

Loss of alkoxide ion to reform carbonyl

Acidic workup

If the claisen condensation reaction takes place within the same molecule means a ring is formed. This is known as intramolecular claisen condensation (Dieckmann cyclization)

Please note the base considered for the reaction should have the same alkoxide group which is present in the ester of the starting material to avoid transesterification.

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21.4, Problem 28CC

Interpretation Introduction