The detailed mechanisms of the given reactions are to be predicted. Concept introduction: A mechanism involves the collection of all those steps that occur in a reaction. Ester formation occurs between carboxylic acid and alcohol in acidic medium. It involves protonation of the carbonyl group of carboxylic acid, and then attack of hydroxyl oxygen of alcohol on the carbonyl carbon. It involves the formation of water as another product. The amide bond contains a carbonyl group bonded to an amino group. The amide bond is a reaction product of carboxylic acid, acid chlorides or esters with primary amines . It occurs by nucleophilic attack of the carbonyl carbon by an amine group. Hydrolysis of the cyanide group in acidic medium results in the formation of the carboxylic group. The reaction occurs in presence of mineral acid and proceeds via the formation of amide as an intermediate.

Question

(a) (b) (c) Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw the starting material(s), key reagent and a full reaction mechanism including an explanation of the observed geometry. Which of the following (B) and (C) will favour the enol form? Briefly explain your reasoning. Predict the product(s) and provide a mechanism for each of the following transformations: (i) (ii) OMe OMe Base OEt NaOEt

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 17, Problem 33P

Interpretation Introduction

Interpretation:

The detailed mechanisms of the given reactions are to be predicted.

Concept introduction:

A mechanism involves the collection of all those steps that occur in a reaction.

Ester formation occurs between carboxylic acid and alcohol in acidic medium. It involves protonation of the carbonyl group of carboxylic acid, and then attack of hydroxyl oxygen of alcohol on the carbonyl carbon. It involves the formation of water as another product.

The amide bond contains a carbonyl group bonded to an amino group. The amide bond is a reaction product of carboxylic acid, acid chlorides or esters with primary amines. It occurs by nucleophilic attack of the carbonyl carbon by an amine group.

Hydrolysis of the cyanide group in acidic medium results in the formation of the carboxylic group. The reaction occurs in presence of mineral acid and proceeds via the formation of amide as an intermediate.

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(a) (b) (c) Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw the starting material(s), key reagent and a full reaction mechanism including an explanation of the observed geometry. Which of the following (B) and (C) will favour the enol form? Briefly explain your reasoning. Predict the product(s) and provide a mechanism for each of the following transformations: (i) (ii) OMe OMe Base OEt NaOEt

Suggest the most appropriate method for each of the following laboratory syntheses.(a) cyclopentanol ¡ cyclopentanone

Each of the following can be prepared by an intramolecular aldol condensation of a diketone. Apply retrosynthetic analysis to deduce the structure of the diketone in each case.

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 17, Problem 33P

Interpretation Introduction

Interpretation:

The detailed mechanisms of the given reactions are to be predicted.

Concept introduction:

A mechanism involves the collection of all those steps that occur in a reaction.

Ester formation occurs between carboxylic acid and alcohol in acidic medium. It involves protonation of the carbonyl group of carboxylic acid, and then attack of hydroxyl oxygen of alcohol on the carbonyl carbon. It involves the formation of water as another product.

The amide bond contains a carbonyl group bonded to an amino group. The amide bond is a reaction product of carboxylic acid, acid chlorides or esters with primary amines. It occurs by nucleophilic attack of the carbonyl carbon by an amine group.

Hydrolysis of the cyanide group in acidic medium results in the formation of the carboxylic group. The reaction occurs in presence of mineral acid and proceeds via the formation of amide as an intermediate.

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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 17, Problem 33P

Interpretation Introduction

Interpretation:

The detailed mechanisms of the given reactions are to be predicted.

Concept introduction:

A mechanism involves the collection of all those steps that occur in a reaction.

Ester formation occurs between carboxylic acid and alcohol in acidic medium. It involves protonation of the carbonyl group of carboxylic acid, and then attack of hydroxyl oxygen of alcohol on the carbonyl carbon. It involves the formation of water as another product.

The amide bond contains a carbonyl group bonded to an amino group. The amide bond is a reaction product of carboxylic acid, acid chlorides or esters with primary amines. It occurs by nucleophilic attack of the carbonyl carbon by an amine group.

Hydrolysis of the cyanide group in acidic medium results in the formation of the carboxylic group. The reaction occurs in presence of mineral acid and proceeds via the formation of amide as an intermediate.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 17, Problem 33P

Interpretation Introduction