The structure of the lactone formed as the final product in the given reaction and havinga molecular formula C 12 H 16 O 2 , is to be determined. Concept Introduction: Carboxylic acids in presence of the reagent NaH, THF followed by LDA yields anacid dianions in which the negative charge resides on both the oxygen atoms in the original carboxylic acid . However, the dianion formed has carbanionic character and it can potentially act as anucleophile to create a new carbon-carbon single bond. The reactions of dianions with epoxides generate a hydroxyl acid. The carbon atom in the dianion attacks on the less hindered carbon atom of the epoxide to yield a hydroxy acid derivative. Thus, there will be a new carbon-carbon single bond formed between the carbon atom in the dianion and the less hindered carbon atom in the epoxide. The hydroxy acid generated can be then cyclized to yield a lactone, this creates a new carbon-oxygen single bond between carbonyl carbon in the carboxylic acid group and the oxygen atom in the epoxide.

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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 21, Problem 60DSP

Interpretation Introduction

Interpretation:

The structure of the lactone formed as the final product in the given reaction and havinga molecular formula C12H16O2, is to be determined.

Concept Introduction:

Carboxylic acids in presence of the reagent NaH, THF followed by LDA yields anacid dianions in which the negative charge resides on both the oxygen atoms in the original carboxylic acid.

However, the dianion formed has carbanionic character and it can potentially act as anucleophile to create a new carbon-carbon single bond.

The reactions of dianions with epoxides generate a hydroxyl acid. The carbon atom in the dianion attacks on the less hindered carbon atom of the epoxide to yield a hydroxy acid derivative. Thus, there will be a new carbon-carbon single bond formed between the carbon atom in the dianion and the less hindered carbon atom in the epoxide.

The hydroxy acid generated can be then cyclized to yield a lactone, this creates a new carbon-oxygen single bond between carbonyl carbon in the carboxylic acid group and the oxygen atom in the epoxide.

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If a reaction occurs, what would be the major products? Please include a detailed explanation as well as a drawing showing how the reaction occurs and what the final product is.

Answer 2

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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 21, Problem 60DSP

Interpretation Introduction

Interpretation:

The structure of the lactone formed as the final product in the given reaction and havinga molecular formula C12H16O2, is to be determined.

Concept Introduction:

Carboxylic acids in presence of the reagent NaH, THF followed by LDA yields anacid dianions in which the negative charge resides on both the oxygen atoms in the original carboxylic acid.

However, the dianion formed has carbanionic character and it can potentially act as anucleophile to create a new carbon-carbon single bond.

The reactions of dianions with epoxides generate a hydroxyl acid. The carbon atom in the dianion attacks on the less hindered carbon atom of the epoxide to yield a hydroxy acid derivative. Thus, there will be a new carbon-carbon single bond formed between the carbon atom in the dianion and the less hindered carbon atom in the epoxide.

The hydroxy acid generated can be then cyclized to yield a lactone, this creates a new carbon-oxygen single bond between carbonyl carbon in the carboxylic acid group and the oxygen atom in the epoxide.

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Answer 3

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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 21, Problem 60DSP

Interpretation Introduction

Interpretation:

The structure of the lactone formed as the final product in the given reaction and havinga molecular formula C12H16O2, is to be determined.

Concept Introduction:

Carboxylic acids in presence of the reagent NaH, THF followed by LDA yields anacid dianions in which the negative charge resides on both the oxygen atoms in the original carboxylic acid.

However, the dianion formed has carbanionic character and it can potentially act as anucleophile to create a new carbon-carbon single bond.

The reactions of dianions with epoxides generate a hydroxyl acid. The carbon atom in the dianion attacks on the less hindered carbon atom of the epoxide to yield a hydroxy acid derivative. Thus, there will be a new carbon-carbon single bond formed between the carbon atom in the dianion and the less hindered carbon atom in the epoxide.

The hydroxy acid generated can be then cyclized to yield a lactone, this creates a new carbon-oxygen single bond between carbonyl carbon in the carboxylic acid group and the oxygen atom in the epoxide.

Expert Solution & Answer

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Check out a sample textbook solution

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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 21, Problem 60DSP

Interpretation Introduction