For the alkylation of a given compound under two different conditions to form ketoesters A and B, and for each ketoester to form cyclic diketone C and D on treatment with methoxide ion in methanol, The structure of A and B and indicate the conditions used in the alkylation to form the ketoester has to be given. Concept introduction: Lithium diisopropylamide is a strong base. Therefore, it can abstract a proton from α carbon atom of a ketone . Enolate ion is formed. Enolate ion can be a thermodynamic enolate ion or a kinetic enolate ion. Thermodynamic enolate ion is formed at temperature 0 ° C . Kinetic enolate ion is formed at temperature − 7 8 ° C . Kinetic enolate ion is less substituted and thermodynamic enolate ion is more substituted. Ketoester on reaction with base undergoes cyclisation reaction.

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Answer 1

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Chapter 17, Problem 87P

(a)

Interpretation Introduction

Interpretation: For the alkylation of a given compound under two different conditions to form ketoesters A and B, and for each ketoester to form cyclic diketone C and D on treatment with methoxide ion in methanol,

The structure of A and B and indicate the conditions used in the alkylation to form the ketoester has to be given.

Concept introduction: Lithium diisopropylamide is a strong base. Therefore, it can abstract a proton from α carbon atom of a ketone. Enolate ion is formed. Enolate ion can be a thermodynamic enolate ion or a kinetic enolate ion.

Thermodynamic enolate ion is formed at temperature 0 °C. Kinetic enolate ion is formed at temperature −78 °C. Kinetic enolate ion is less substituted and thermodynamic enolate ion is more substituted. Ketoester on reaction with base undergoes cyclisation reaction.

(b)

Interpretation Introduction

Interpretation:
Mechanism for the conversion of keto ester A into cyclic diketone has to be given.

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Answer 2

Question

Chapter 17, Problem 87P

(a)

Interpretation Introduction

Interpretation: For the alkylation of a given compound under two different conditions to form ketoesters A and B, and for each ketoester to form cyclic diketone C and D on treatment with methoxide ion in methanol,

The structure of A and B and indicate the conditions used in the alkylation to form the ketoester has to be given.

Concept introduction: Lithium diisopropylamide is a strong base. Therefore, it can abstract a proton from α carbon atom of a ketone. Enolate ion is formed. Enolate ion can be a thermodynamic enolate ion or a kinetic enolate ion.

Thermodynamic enolate ion is formed at temperature 0 °C. Kinetic enolate ion is formed at temperature −78 °C. Kinetic enolate ion is less substituted and thermodynamic enolate ion is more substituted. Ketoester on reaction with base undergoes cyclisation reaction.

(b)

Interpretation Introduction

Interpretation:
Mechanism for the conversion of keto ester A into cyclic diketone has to be given.

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Answer 3

Question

Chapter 17, Problem 87P

(a)

Interpretation Introduction

Interpretation: For the alkylation of a given compound under two different conditions to form ketoesters A and B, and for each ketoester to form cyclic diketone C and D on treatment with methoxide ion in methanol,

The structure of A and B and indicate the conditions used in the alkylation to form the ketoester has to be given.

Concept introduction: Lithium diisopropylamide is a strong base. Therefore, it can abstract a proton from α carbon atom of a ketone. Enolate ion is formed. Enolate ion can be a thermodynamic enolate ion or a kinetic enolate ion.

Thermodynamic enolate ion is formed at temperature 0 °C. Kinetic enolate ion is formed at temperature −78 °C. Kinetic enolate ion is less substituted and thermodynamic enolate ion is more substituted. Ketoester on reaction with base undergoes cyclisation reaction.

(b)

Interpretation Introduction

Interpretation:
Mechanism for the conversion of keto ester A into cyclic diketone has to be given.

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Answer 4

Question

Chapter 17, Problem 87P

(a)

Interpretation Introduction

Interpretation: For the alkylation of a given compound under two different conditions to form ketoesters A and B, and for each ketoester to form cyclic diketone C and D on treatment with methoxide ion in methanol,

The structure of A and B and indicate the conditions used in the alkylation to form the ketoester has to be given.

Concept introduction: Lithium diisopropylamide is a strong base. Therefore, it can abstract a proton from α carbon atom of a ketone. Enolate ion is formed. Enolate ion can be a thermodynamic enolate ion or a kinetic enolate ion.

Thermodynamic enolate ion is formed at temperature 0 °C. Kinetic enolate ion is formed at temperature −78 °C. Kinetic enolate ion is less substituted and thermodynamic enolate ion is more substituted. Ketoester on reaction with base undergoes cyclisation reaction.

(b)

Interpretation Introduction

Interpretation:
Mechanism for the conversion of keto ester A into cyclic diketone has to be given.

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Answer 5

Chapter 17, Problem 87P

(a)

Interpretation Introduction

Interpretation: For the alkylation of a given compound under two different conditions to form ketoesters A and B, and for each ketoester to form cyclic diketone C and D on treatment with methoxide ion in methanol,

The structure of A and B and indicate the conditions used in the alkylation to form the ketoester has to be given.

Concept introduction: Lithium diisopropylamide is a strong base. Therefore, it can abstract a proton from α carbon atom of a ketone. Enolate ion is formed. Enolate ion can be a thermodynamic enolate ion or a kinetic enolate ion.

Thermodynamic enolate ion is formed at temperature 0 °C. Kinetic enolate ion is formed at temperature −78 °C. Kinetic enolate ion is less substituted and thermodynamic enolate ion is more substituted. Ketoester on reaction with base undergoes cyclisation reaction.

(b)

Interpretation Introduction

Interpretation:
Mechanism for the conversion of keto ester A into cyclic diketone has to be given.

Answer 6

Chapter 17, Problem 87P

(a)

Interpretation Introduction

Interpretation: For the alkylation of a given compound under two different conditions to form ketoesters A and B, and for each ketoester to form cyclic diketone C and D on treatment with methoxide ion in methanol,

The structure of A and B and indicate the conditions used in the alkylation to form the ketoester has to be given.

Concept introduction: Lithium diisopropylamide is a strong base. Therefore, it can abstract a proton from α carbon atom of a ketone. Enolate ion is formed. Enolate ion can be a thermodynamic enolate ion or a kinetic enolate ion.

Thermodynamic enolate ion is formed at temperature 0 °C. Kinetic enolate ion is formed at temperature −78 °C. Kinetic enolate ion is less substituted and thermodynamic enolate ion is more substituted. Ketoester on reaction with base undergoes cyclisation reaction.

Answer 7

Chapter 17, Problem 87P

(a)

Interpretation Introduction

Interpretation: For the alkylation of a given compound under two different conditions to form ketoesters A and B, and for each ketoester to form cyclic diketone C and D on treatment with methoxide ion in methanol,

The structure of A and B and indicate the conditions used in the alkylation to form the ketoester has to be given.

Concept introduction: Lithium diisopropylamide is a strong base. Therefore, it can abstract a proton from α carbon atom of a ketone. Enolate ion is formed. Enolate ion can be a thermodynamic enolate ion or a kinetic enolate ion.

Thermodynamic enolate ion is formed at temperature 0 °C. Kinetic enolate ion is formed at temperature −78 °C. Kinetic enolate ion is less substituted and thermodynamic enolate ion is more substituted. Ketoester on reaction with base undergoes cyclisation reaction.

Answer 8

(b)

Interpretation Introduction

Interpretation:
Mechanism for the conversion of keto ester A into cyclic diketone has to be given.

Answer 9

(b)

Interpretation Introduction

Interpretation:
Mechanism for the conversion of keto ester A into cyclic diketone has to be given.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 17.1 - Prob. 1P Ch. 17.1 - Prob. 2P Ch. 17.1 - Prob. 3P Ch. 17.1 - Prob. 4P Ch. 17.1 - Rank the compounds in each of the following groups...Ch. 17.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 17.3 - Draw the enol tautomers for each of the following...Ch. 17.3 - Prob. 8P Ch. 17.4 - Prob. 9P Ch. 17.4 - Prob. 10P

Solution Summary: The author explains the structure of A and B and the conditions used in the alkylation to form the ketoester.

Concept explainers

Interpretation:
Mechanism for the conversion of keto ester A into cyclic diketone has to be given.

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Chapter 17 Solutions

Solution Summary: The author explains the structure of A and B and the conditions used in the alkylation to form the ketoester.

Concept explainers

Interpretation: Mechanism for the conversion of keto ester A into cyclic diketone has to be given.

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Chapter 17 Solutions

Interpretation:
Mechanism for the conversion of keto ester A into cyclic diketone has to be given.