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

1. For an unknown compound with a molecular formula of C8H100: a. What is the DU? (show your work) b. Solve the structure and assign each of the following spectra. 8 6 2 ō (ppm) 4 2 0 200 150 100 50 ō (ppm) LOD D 4000 3000 2000 1500 1000 500 HAVENUMBERI -11

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 32P

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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1. For an unknown compound with a molecular formula of C8H100: a. What is the DU? (show your work) b. Solve the structure and assign each of the following spectra. 8 6 2 ō (ppm) 4 2 0 200 150 100 50 ō (ppm) LOD D 4000 3000 2000 1500 1000 500 HAVENUMBERI -11

16. The proton NMR spectral information shown in this problem is for a compound with formula CioH,N. Expansions are shown for the region from 8.7 to 7.0 ppm. The normal carbon-13 spec- tral results, including DEPT-135 and DEPT-90 results, are tabulated: 7 J Normal Carbon DEPT-135 DEPT-90 19 ppm Positive No peak 122 Positive Positive cus и 124 Positive Positive 126 Positive Positive 128 No peak No peak 4° 129 Positive Positive 130 Positive Positive (144 No peak No peak 148 No peak No peak 150 Positive Positive してし

3. Propose a synthesis for the following transformation. Do not draw an arrow-pushing mechanism below, but make sure to draw the product of each proposed step (3 points). + En CN CN

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 32P

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

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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 17, Problem 32P

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 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 32P

Interpretation Introduction