Propose an efficient synthesis of 2-propylcyclohexanone using 1,7-heptanediol and propyl iodide. 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. Alkylation of the Dieckmann cyclization product followed by hydrolysis and decarboxylation at high temperature results in the formation of the required product.

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Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.5, Problem 43ATS

Interpretation Introduction

Interpretation:

Propose an efficient synthesis of 2-propylcyclohexanone using 1,7-heptanediol and propyl iodide.

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.

Alkylation of the Dieckmann cyclization product followed by hydrolysis and decarboxylation at high temperature results in the formation of the required product.

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#1. Retro-Electrochemical Reaction: A ring has been made, but the light is causing the molecule to un- cyclize. Undo the ring into all possible molecules. (2pts, no partial credit) hv

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I have a question about this problem involving mechanisms and drawing curved arrows for acids and bases. I know we need to identify the nucleophile and electrophile, but are there different types of reactions? For instance, what about Grignard reagents and other types that I might not be familiar with? Can you help me with this? I want to identify the names of the mechanisms for problems 1-14, such as Gilman reagents and others. Are they all the same? Also, could you rewrite it so I can better understand? The handwriting is pretty cluttered. Additionally, I need to label the nucleophile and electrophile, but my main concern is whether those reactions differ, like the "Brønsted-Lowry acid-base mechanism, Lewis acid-base mechanism, acid-catalyzed mechanisms, acid-catalyzed reactions, base-catalyzed reactions, nucleophilic substitution mechanisms (SN1 and SN2), elimination reactions (E1 and E2), organometallic mechanisms, and so forth."

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.5, Problem 43ATS

Interpretation Introduction

Interpretation:

Propose an efficient synthesis of 2-propylcyclohexanone using 1,7-heptanediol and propyl iodide.

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.

Alkylation of the Dieckmann cyclization product followed by hydrolysis and decarboxylation at high temperature results in the formation of the required product.

Expert Solution & Answer

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Check out a sample textbook solution

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.5, Problem 43ATS

Interpretation Introduction

Interpretation:

Propose an efficient synthesis of 2-propylcyclohexanone using 1,7-heptanediol and propyl iodide.

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.

Alkylation of the Dieckmann cyclization product followed by hydrolysis and decarboxylation at high temperature results in the formation of the required product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 22.5, Problem 43ATS

Interpretation Introduction