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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Alkylation of the following compound with methyl iodide under two different conditions forms two different ketoesters (A and B). Each ketoester formsa cyclic diketone (C and D) when treated with methoxide ion in methanol. a. Draw the structures of A and B, and indicate the conditions used in the alkylation reaction that cause that ketoester to be formed.b. Draw the mechanism for the conversion of A to C.

When 1-methoxy-2-methylpropene is treated with HCl, the major product is 1-chloro-1-methoxy-2-methylpropane. Although this reaction proceeds via an iconic mechanism, the Cl is ultimately positioned at the less substituted carbon. Draw a mechanism with this outcome and explain why the less substituted carbonation intermediate is more stable. Explanation: The less substituted carbonation has better stabilization because of a. resonance b. electron donation by the methyl groups c. reduced steric hindrance d. electron withdrawal by the methyl groups while the more substituted carbon is only stabilized by: a. resonance b. electron donation by the methyl groups c. reduced steric hindrance d. electron withdrawal by the methyl groups

7. When the following ketone is treated with sodium hydroxide, two different enolates can form. a. Draw the two enolates, including an arrow pushing mechanism for their formation and any relevant resonance structures. NaOH b. Which enolate is favored when using sodium hydroxide as the base? Explain. c. Predict the product of the reaction and include an arrow-pushing mechanism. 1. NaOH 2. Br

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.