A structure for atropine (C 17 H 23 NO 3 ) is to be proposed from the following observations: i) On basic hydrolysis atropine yields tropic acid C 6 H 5 CH(CH 2 OH)COOH and tropine (C 8 H 15 NO). ii) Tropine is an optically inactive alcohol that yields tropidene on dehydration with H 2 SO 4 . Concept introduction: Esters when hydrolyzed with bases yield alcohols and carboxylic acids. Alcohols when treated with H 2 SO 4 give alkenes. Symmetrical compounds are optically inactive. To predict: A structure for atropine (C 17 H 23 NO 3 ) from the following observations: i) On basic hydrolysis atropine yields tropic acid C 6 H 5 CH(CH 2 OH)COOH and tropine (C 8 H 15 NO). ii) Tropine is an optically inactive alcohol that yields tropidene on dehydration with H 2 SO 4 . Answer: Structure of atropine is Explanation: Atropine gives tropic acid and an alcohol, tropine when hydrolyzed in the presence of bases. Hence it must be an ester. Tropine upon dehydration gives tropidene. Hence structure of tropine (optically inactive) can be obtained by adding water to the structure of tropidene. The formation of the ester linkage between the OH of atropine and COOH of tropic acid gives atropine. The reactions can be represented as below. Conclusion: Structure of atropine is

Question

1. Arrange the following in order of increasing bond energy (lowest bond energy first, highest bond energy last). Provide your rationale. C=C, C-F, C=C, C-N, C-C List the bond order for each example.

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 24.SE, Problem 75AP

Interpretation Introduction

Interpretation:

A structure for atropine (C₁₇H₂₃NO₃) is to be proposed from the following observations: i) On basic hydrolysis atropine yields tropic acid C₆H₅CH(CH₂OH)COOH and tropine (C₈H₁₅NO). ii) Tropine is an optically inactive alcohol that yields tropidene on dehydration with H₂SO₄.

Concept introduction:

Esters when hydrolyzed with bases yield alcohols and carboxylic acids. Alcohols when treated with H₂SO₄ give alkenes. Symmetrical compounds are optically inactive.

To predict:

A structure for atropine (C₁₇H₂₃NO₃) from the following observations: i) On basic hydrolysis atropine yields tropic acid C₆H₅CH(CH₂OH)COOH and tropine (C₈H₁₅NO). ii) Tropine is an optically inactive alcohol that yields tropidene on dehydration with H₂SO₄.

Answer:

Structure of atropine is

Explanation:

Atropine gives tropic acid and an alcohol, tropine when hydrolyzed in the presence of bases. Hence it must be an ester. Tropine upon dehydration gives tropidene. Hence structure of tropine (optically inactive) can be obtained by adding water to the structure of tropidene.

The formation of the ester linkage between the OH of atropine and COOH of tropic acid gives atropine. The reactions can be represented as below.

Conclusion:

Structure of atropine is

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1. Arrange the following in order of increasing bond energy (lowest bond energy first, highest bond energy last). Provide your rationale. C=C, C-F, C=C, C-N, C-C List the bond order for each example.

What is the major enolate formed when treated with LDA? And why that one?

4. Calculate the total number of sigma bonds and total number of pi bonds in each of the following compounds. a. HH :D: +1 I H-N-C-C-O-H I H b. HH H Н :N=C-C-C=C-CEC-H :0: total o H-C-H H-C = `C-H I H. 11 H-C = C= CH H total o total π total π 1 H

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 24.SE, Problem 75AP

Interpretation Introduction

Interpretation:

A structure for atropine (C₁₇H₂₃NO₃) is to be proposed from the following observations: i) On basic hydrolysis atropine yields tropic acid C₆H₅CH(CH₂OH)COOH and tropine (C₈H₁₅NO). ii) Tropine is an optically inactive alcohol that yields tropidene on dehydration with H₂SO₄.

Concept introduction:

Esters when hydrolyzed with bases yield alcohols and carboxylic acids. Alcohols when treated with H₂SO₄ give alkenes. Symmetrical compounds are optically inactive.

To predict:

A structure for atropine (C₁₇H₂₃NO₃) from the following observations: i) On basic hydrolysis atropine yields tropic acid C₆H₅CH(CH₂OH)COOH and tropine (C₈H₁₅NO). ii) Tropine is an optically inactive alcohol that yields tropidene on dehydration with H₂SO₄.

Answer:

Structure of atropine is

Explanation:

Atropine gives tropic acid and an alcohol, tropine when hydrolyzed in the presence of bases. Hence it must be an ester. Tropine upon dehydration gives tropidene. Hence structure of tropine (optically inactive) can be obtained by adding water to the structure of tropidene.

The formation of the ester linkage between the OH of atropine and COOH of tropic acid gives atropine. The reactions can be represented as below.

Conclusion:

Structure of atropine is

Expert Solution & Answer

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See solution

Check out sample textbook solution

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 24.SE, Problem 75AP

Interpretation Introduction

Interpretation:

A structure for atropine (C₁₇H₂₃NO₃) is to be proposed from the following observations: i) On basic hydrolysis atropine yields tropic acid C₆H₅CH(CH₂OH)COOH and tropine (C₈H₁₅NO). ii) Tropine is an optically inactive alcohol that yields tropidene on dehydration with H₂SO₄.

Concept introduction:

Esters when hydrolyzed with bases yield alcohols and carboxylic acids. Alcohols when treated with H₂SO₄ give alkenes. Symmetrical compounds are optically inactive.

To predict:

A structure for atropine (C₁₇H₂₃NO₃) from the following observations: i) On basic hydrolysis atropine yields tropic acid C₆H₅CH(CH₂OH)COOH and tropine (C₈H₁₅NO). ii) Tropine is an optically inactive alcohol that yields tropidene on dehydration with H₂SO₄.

Answer:

Structure of atropine is

Explanation:

Atropine gives tropic acid and an alcohol, tropine when hydrolyzed in the presence of bases. Hence it must be an ester. Tropine upon dehydration gives tropidene. Hence structure of tropine (optically inactive) can be obtained by adding water to the structure of tropidene.

The formation of the ester linkage between the OH of atropine and COOH of tropic acid gives atropine. The reactions can be represented as below.

Conclusion:

Structure of atropine is

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 24.SE, Problem 75AP

Interpretation Introduction