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.

Question

Want to see the full answer?

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Identify the starting material in the following reaction. Click the "draw structure" button to launch the drawing utility. draw structure ... [1] 0 3 C10H18 [2] CH3SCH3 H

In an equilibrium mixture of the formation of ammonia from nitrogen and hydrogen, it is found that PNH3 = 0.147 atm, PN2 = 1.41 atm and Pн2 = 6.00 atm. Evaluate Kp and Kc at 500 °C. 2 NH3 (g) N2 (g) + 3 H₂ (g) K₂ = (PN2)(PH2)³ = (1.41) (6.00)³ = 1.41 x 104

What alkene or alkyne yields the following products after oxidative cleavage with ozone? Click the "draw structure" button to launch the drawing utility. and two equivalents of CH2=O draw structure ...

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Concept explainers

Want to see the full answer?

Chapter 13 Solutions