The structure of compound X in the given reactionis to be determined. Concept Introduction: Cyclic esters are called lactones and are often prepared by the intra-molecular cyclization of hydroxy substituted carboxylic acids . Electrophilic addition to the double bond of unsaturated carboxylic acids gives lactone. The phenylselenolactonization, the electrophilic reagent used is benzeneselenylchloride. Anti addition takes place in this cyclization. A selenoxide is produced by the oxidation of the C 6 H 5 Se substituent. It undergoes elimination to produce a double bond in the lactone by the elimination of the beta hydrogen which is away from the lactone oxygen.

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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 19, Problem 37DSP

Interpretation Introduction

Interpretation:

The structure of compound X in the given reactionis to be determined.

Concept Introduction:

Cyclic esters are called lactones and are often prepared by the intra-molecular cyclization of hydroxy substituted carboxylic acids.

Electrophilic addition to the double bond of unsaturated carboxylic acids gives lactone.

The phenylselenolactonization, the electrophilic reagent used is benzeneselenylchloride.

Anti addition takes place in this cyclization.

A selenoxide is produced by the oxidation of the C6H5Se substituent. It undergoes elimination to produce a double bond in the lactone by the elimination of the beta hydrogen which is away from the lactone oxygen.

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The two reactions that follow involve nucleophilic substitution at an acyl carbon. For each reaction, show the electrophile and the nucleophile in the key bond- forming step, the corresponding tetrahedral addition intermediate, and the leaving group in the bond-breaking step. Write a general mechanistic scheme (use curved arrows to show bond-making and bond-breaking processes) for these reactions, keeping in mind that acid- and base-catalyzed processes will differ in their timing of proton transfers. 00 || || PhCOCPh+ C₂H5OH 00 |||| PhCOCPh+ 2 CH3NH H₂SO4 cat. O PhCOC₂H5+ PhCO₂H PhCNCHg + CH3NH PhCO

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 19, Problem 37DSP

Interpretation Introduction

Interpretation:

The structure of compound X in the given reactionis to be determined.

Concept Introduction:

Cyclic esters are called lactones and are often prepared by the intra-molecular cyclization of hydroxy substituted carboxylic acids.

Electrophilic addition to the double bond of unsaturated carboxylic acids gives lactone.

The phenylselenolactonization, the electrophilic reagent used is benzeneselenylchloride.

Anti addition takes place in this cyclization.

A selenoxide is produced by the oxidation of the C6H5Se substituent. It undergoes elimination to produce a double bond in the lactone by the elimination of the beta hydrogen which is away from the lactone oxygen.

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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 19, Problem 37DSP

Interpretation Introduction

Interpretation:

The structure of compound X in the given reactionis to be determined.

Concept Introduction:

Cyclic esters are called lactones and are often prepared by the intra-molecular cyclization of hydroxy substituted carboxylic acids.

Electrophilic addition to the double bond of unsaturated carboxylic acids gives lactone.

The phenylselenolactonization, the electrophilic reagent used is benzeneselenylchloride.

Anti addition takes place in this cyclization.

A selenoxide is produced by the oxidation of the C6H5Se substituent. It undergoes elimination to produce a double bond in the lactone by the elimination of the beta hydrogen which is away from the lactone oxygen.

Expert Solution & Answer

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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 19, Problem 37DSP

Interpretation Introduction