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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Part V. Label ad match the carbons in compounds Jane and Diane w/ the corresponding peak no. in the Spectra (Note: use the given peak no. To label the carbons, other peak no are intentionally omitted) 7 4 2 -0.13 -0.12 -0.11 -0.10 -0.08 8 CI Jane 1 -0.09 5 210 200 190 180 170 160 150 140 130 120 110 100 -8 90 f1 (ppm) 11 8 172.4 172.0 f1 (ppr HO CI NH Diane 7 3 11 80 80 -80 -R 70 60 60 2 5 -8 50 40 8. 170 160 150 140 130 120 110 100 90 -0 80 70 20 f1 (ppm) 15 30 -20 20 -60 60 -0.07 -0.06 -0.05 -0.04 -0.03 -0.02 -0.01 -0.00 -0.01 10 -0.17 16 15 56 16 -0.16 -0.15 -0.14 -0.13 -0.12 -0.11 -0.10 -0.09 -0.08 -0.07 -0.06 -0.05 -0.04 17.8 17.6 17.4 17.2 17.0 f1 (ppm) -0.03 -0.02 550 106 40 30 20 20 -0.01 -0.00 F-0.01 10 0

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

See solution

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