To determine the number of deuterium atoms that are incorporated in palmitic acid if CD 3 COSR and nondeuterated malonyl thioester are used as starting materials. Concept introduction: For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester. The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

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Answer 1

Question

Chapter 13, Problem 33P

(a)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if CD3COSR and nondeuterated malonyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

(b)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if −OOCCD2COSR and nondeuterated acetyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

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Redraw the tripeptide with or without its acidic hydrogensto demonstrate where the total charge of -2 comes from: *see image

2. Consider the data below to answer the following questions. Cyanohydrins are important intermediates in the synthesis of α-hydroxycarboxylic acids from ketones and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated. OH CH-COOH 0 HO CN C H30* C. H H HC N NaOH H₂O C=O 0 cyanohydrin H + NaCN + H₂O

Answer 2

Question

Chapter 13, Problem 33P

(a)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if CD3COSR and nondeuterated malonyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

(b)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if −OOCCD2COSR and nondeuterated acetyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

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Answer 3

Question

Chapter 13, Problem 33P

(a)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if CD3COSR and nondeuterated malonyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

(b)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if −OOCCD2COSR and nondeuterated acetyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

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Answer 4

Question

Chapter 13, Problem 33P

(a)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if CD3COSR and nondeuterated malonyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

(b)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if −OOCCD2COSR and nondeuterated acetyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

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Answer 5

Chapter 13, Problem 33P

(a)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if CD3COSR and nondeuterated malonyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

(b)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if −OOCCD2COSR and nondeuterated acetyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

Answer 6

Chapter 13, Problem 33P

(a)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if CD3COSR and nondeuterated malonyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

Answer 7

Chapter 13, Problem 33P

(a)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if CD3COSR and nondeuterated malonyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

Answer 8

(b)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if −OOCCD2COSR and nondeuterated acetyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

Answer 9

(b)

Interpretation Introduction

Interpretation:

To determine the number of deuterium atoms that are incorporated in palmitic acid if −OOCCD2COSR and nondeuterated acetyl thioester are used as starting materials.

Concept introduction:

For the synthesis of arachidic acid, in first step acetyl thioester and malonyl thioester undergoes Claisen condensation. The product of Claisen condensation undergoes reduction, dehydration and a second reduction to form a four-carbon thioester.

The four carbon thioester combines with another molecule of malonyl thioester and undergoes Claisen condensation, reduction, dehydration and a second reduction to form a six carbon thioester. The reaction can proceed to form a fatty acid of an even number of carbon atoms and repetition of sequence adds two carbon.

Answer 10

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Answer 12

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Answer 13

Ch. 13.1 - Identify the most acidic hydrogen in each...Ch. 13.1 - Prob. 2P Ch. 13.1 - Prob. 3P Ch. 13.1 - Prob. 4P Ch. 13.1 - Explain why HO cannot remove a proton from the...Ch. 13.2 - Prob. 6P Ch. 13.2 - Prob. 7P Ch. 13.3 - Prob. 8P Ch. 13.3 - Prob. 9P Ch. 13.3 - Prob. 10P

Solution Summary: The author explains how the number of deuterium atoms that are incorporated in palmitic acid is determined if and nondeuterated malonyl thioester are used as starting materials.

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