Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 16, Problem 16.10P

Neuroprotectin D1 (NPD1) is synthesized in the body from highly unsaturated essential fatty acids. NPD1 is a potent natural anti-inflammatory agent.

Chapter 16, Problem 16.10P, Problem 16.11 Neuroprotectin D1 (NPD1) is synthesized in the body from highly unsaturated essential

NPD1

a. Label each double bond as conjugated or isolated.

b. Label each double bond as E or Z.

c. For each conjugated system, label the given conformation as s-cis or s-trans.

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: Neuroprotectin D1 is synthesized in the body from highly unsaturated essential fatty acids. NPD1 is a potent natural anti-inflammatory agent. The each double bond in NPD1 is to be labeled as conjugated or isolated.

Concept introduction: Diene is a hydrocarbon that contains two C=C double bonds in a compound.

Conjugated diene consists of two double bonds that are separated by a single bond, whereas isolated diene also consists of two double bond but they are separated by two more carbon atoms.

The example that shows the basic difference between conjugated diene and isolated diene is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  1

Figure 1

In conjugated diene, electrons in the pi bonds are delocalized, whereas in isolated diene, electrons in the pi bonds are localized.

Answer to Problem 16.10P

The each double bond in NPD1 as conjugated and isolated diene is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  2

Figure 3

The double bond present between C4C5, C7C8 and C19C20 are isolated, whereas double bond present between C11C12, C13C14 and C15C16 are conjugated.

Explanation of Solution

The given structure of NPD1 is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  3

Figure 2

Diene is a hydrocarbon that contains two C=C double bonds in a compound.

Conjugated diene consists of two double bonds that are separated by a single bond, whereas isolated diene also consists of two double bond but they are separated by two more carbon atoms. Therefore, carbon atoms of a conjugated double bond are sp2 hybridized, whereas carbon atoms of a isolated double bond is one or more sp3 hybridized.

The each double bond in NPD1 as conjugated and isolated diene is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  4

Figure 3

The double bond present between C4C5, C7C8 and C19C20 are isolated, whereas double bond present between C11C12, C13C14 and C15C16 are conjugated.

Conclusion

The each double bond in NPD1 as conjugated or isolated is rightfully stated.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: Neuroprotectin D1 is synthesized in the body from highly unsaturated essential fatty acids. NPD1 is a potent natural anti-inflammatory agent. The each double bond in NPD1 is to be labeled as E or Z.

Concept introduction: The prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is Z isomer.

Answer to Problem 16.10P

The each double bond in NPD1 as conjugated and isolated diene is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  5

Figure 4

The double bond present between C4C5, C7C8 and C19C20 have Z conformation, whereas double bond present between C11C12, C13C14 are have E conformation.

Explanation of Solution

The given structure of NPD1 is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  6

Figure 2

The prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is Z isomer.

The each double bond in NPD1 as conjugated and isolated diene is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  7

Figure 4

The double bond present between C4C5, C7C8 and C19C20 have Z conformation, whereas double bond present between C11C12, C13C14 are have E conformation.

Conclusion

The each double bond in NPD1 as E or Z is rightfully stated.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: Neuroprotectin D1 is synthesized in the body from highly unsaturated essential fatty acids. NPD1 is a potent natural anti-inflammatory agent. For each conjugated system in NPD1 is to be labeled as scis or strans conformation.

Concept introduction: “If the two double bonds are on the same side of the single bond joining the two double bonds, then it is known as scis conformation, whereas if the two double bonds are on the opposite side of the single bond joining the two double bonds, then it is known as strans conformation.”

Answer to Problem 16.10P

The each double bond in NPD1 as conjugated and isolated diene is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  8

Figure 3

The double bond present between C11C12, C13C14 and C15C16 are conjugated. The double bonds between C11C12 and C13C14 are on same side of the single bond C12C13 and thus, have scis conformation.

The double bonds between C13C14 and C15C16 are on opposite side of the single bond C14C15 and thus, have strans conformation.

Explanation of Solution

The given structure of NPD1 is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  9

Figure 2

“If the two double bonds are on the same side of the single bond joining the two double bonds, then it is known as scis conformation, whereas if the two double bonds are on the opposite side of the single bond joining the two double bonds, then it is known as strans conformation.”

The each double bond in NPD1 as conjugated and isolated diene is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  10

Figure 3

The double bond present between C11C12, C13C14 and C15C16 are conjugated. The double bonds between C11C12 and C13C14 are on same side of the single bond C12C13 and thus, have scis conformation.

The double bonds between C13C14 and C15C16 are on opposite side of the single bond C14C15 and thus, have strans conformation.

Conclusion

The scis and strans conformation for each conjugated system in NPD1 is rightfully stated.

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Chapter 16 Solutions

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