Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 31, Problem 31.27P

Classify each terpene and terpenoid in Problem 31.26 (e.g., as a monoterpene, sesquiterpene, etc.).

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The terpene and terpenoid are to be classified as monoterpene, sesquiterpene, etc.

Concept introduction: Terpenes are naturally occurring compounds that are present in plants and animals. Terpenes contain one or more isoprene units. Terpenoids are derivatives of terpenes with oxygen containing functional group such as carbonyl groups. Monoterpenes contain two isoprene units, sesquiterpene contain three isoprene units etc.

Answer to Problem 31.27P

Neral is classified as monoterpene.

Explanation of Solution

The structure of isoprene is,

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  1

Figure 1

The isoprene unit contains four carbon atoms in the long chain and one carbon atom in branch. Isoprene unit in a terpene consists of carbon-carbon sigma or pi bonds.

The isoprene units in the given compound are shown below.

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  2

Figure 2

The highlighted bonds represent the isoprene unit. There are two isoprene units present in the given compound. Neral is classified as monoterpene.

Conclusion

Neral is classified as monoterpene.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The terpene and terpenoid are to be classified as monoterpene, sesquiterpene, etc.

Concept introduction: Terpenes are naturally occurring compounds that are present in plants and animals. Terpenes contain one or more isoprene units. Terpenoids are derivatives of terpenes with oxygen containing functional group such as carbonyl groups. Monoterpenes contain two isoprene units, sesquiterpene contain three isoprene units etc.

Answer to Problem 31.27P

Carvone is classified as monoterpene.

Explanation of Solution

The structure of isoprene is,

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  3

Figure 1

The isoprene unit contains four carbon atoms in the long chain and one carbon atom in branch. Isoprene unit in a terpene consists of carbon-carbon sigma or pi bonds.

The isoprene units in the given compound are shown below.

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  4

Figure 3

The highlighted bonds represent the isoprene unit. There are two isoprene units present in the given compound. Carvone is classified as monoterpene.

Conclusion

Carvone is classified as monoterpene.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The terpene and terpenoid are to be classified as monoterpene, sesquiterpene, etc.

Concept introduction: Terpenes are naturally occurring compounds that are present in plants and animals. Terpenes contain one or more isoprene units. Terpenoids are derivatives of terpenes with oxygen containing functional group such as carbonyl groups. Monoterpenes contain two isoprene units, sesquiterpene contain three isoprene units etc.

Answer to Problem 31.27P

Lycopene is classified as tetraterpene.

Explanation of Solution

The structure of isoprene is,

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  5

Figure 1

The isoprene unit contains four carbon atoms in the long chain and one carbon atom in branch. Isoprene unit in a terpene consists of carbon-carbon sigma or pi bonds.

The isoprene units in the given compound are shown below.

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  6

Figure 4

The highlighted bonds represent the isoprene unit. There are eight isoprene units present in the given compound. Lycopene is classified as tetraterpene.

Conclusion

Lycopene is classified as tetraterpene.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The terpene and terpenoid are to be classified as monoterpene, sesquiterpene, etc.

Concept introduction: Terpenes are naturally occurring compounds that are present in plants and animals. Terpenes contain one or more isoprene units. Terpenoids are derivatives of terpenes with oxygen containing functional group such as carbonyl groups. Monoterpenes contain two isoprene units, sesquiterpene contain three isoprene units etc.

Answer to Problem 31.27P

The β-carotene is classified as tetraterpene.

Explanation of Solution

The structure of isoprene is,

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  7

Figure 1

The isoprene unit contains four carbon atoms in the long chain and one carbon atom in branch. Isoprene unit in a terpene consists of carbon-carbon sigma or pi bonds.

The isoprene units in the given compound are shown below.

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  8

Figure 5

The highlighted bonds represent the isoprene unit. There are eight isoprene units present in the given compound. The β-carotene is classified as tetraterpene.

Conclusion

The β-carotene is classified as tetraterpene.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The terpene and terpenoid are to be classified as monoterpene, sesquiterpene, etc.

Concept introduction: Terpenes are naturally occurring compounds that are present in plants and animals. Terpenes contain one or more isoprene units. Terpenoids are derivatives of terpenes with oxygen containing functional group such as carbonyl groups. Monoterpenes contain two isoprene units, sesquiterpene contain three isoprene units etc.

Answer to Problem 31.27P

Patchouli alcohol is classified as sesquiterpene.

Explanation of Solution

The structure of isoprene is,

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  9

Figure 1

The isoprene unit contains four carbon atoms in the long chain and one carbon atom in branch. Isoprene unit in a terpene consists of carbon-carbon sigma or pi bonds.

The isoprene units in the given compound are shown below.

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  10

Figure 6

The highlighted bonds represent the isoprene unit. There are three isoprene units present in the given compound. Patchouli alcohol is classified as sesquiterpene.

Conclusion

Patchouli alcohol is classified as sesquiterpene.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The terpene and terpenoid are to be classified as monoterpene, sesquiterpene, etc.

Concept introduction: Terpenes are naturally occurring compounds that are present in plants and animals. Terpenes contain one or more isoprene units. Terpenoids are derivatives of terpenes with oxygen containing functional group such as carbonyl groups. Monoterpenes contain two isoprene units, sesquiterpene contain three isoprene units etc.

Answer to Problem 31.27P

Periplanone B is classified as sesquiterpene.

Explanation of Solution

The structure of isoprene is,

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  11

Figure 1

The isoprene unit contains four carbon atoms in the long chain and one carbon atom in branch. Isoprene unit in a terpene consists of carbon-carbon sigma or pi bonds.

The isoprene units in the given compound are shown below.

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  12

Figure 7

The highlighted bonds represent the isoprene unit. There are three isoprene units present in the given compound. Periplanone B is classified as sesquiterpene.

Conclusion

Periplanone B is classified as sesquiterpene.

Expert Solution
Check Mark
Interpretation Introduction

(g)

Interpretation: The terpene and terpenoid are to be classified as monoterpene, sesquiterpene, etc.

Concept introduction: Terpenes are naturally occurring compounds that are present in plants and animals. Terpenes contain one or more isoprene units. Terpenoids are derivatives of terpenes with oxygen containing functional group such as carbonyl groups. Monoterpenes contain two isoprene units, sesquiterpene contain three isoprene units etc.

Answer to Problem 31.27P

Dextropimaric acid is classified as diterpene.

Explanation of Solution

The structure of isoprene is,

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  13

Figure 1

The isoprene unit contains four carbon atoms in the long chain and one carbon atom in branch. Isoprene unit in a terpene consists of carbon-carbon sigma or pi bonds.

The isoprene units in the given compound are shown below.

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  14

Figure 8

The highlighted bonds represent the isoprene unit. There are four isoprene units present in the given compound. Dextropimaric acid is classified as diterpene.

Conclusion

Dextropimaric acid is classified as diterpene.

Expert Solution
Check Mark
Interpretation Introduction

(h)

Interpretation: The terpene and terpenoid are to be classified as monoterpene, sesquiterpene, etc.

Concept introduction: Terpenes are naturally occurring compounds that are present in plants and animals. Terpenes contain one or more isoprene units. Terpenoids are derivatives of terpenes with oxygen containing functional group such as carbonyl groups. Monoterpenes contain two isoprene units, sesquiterpene contain three isoprene units etc.

Answer to Problem 31.27P

The β-amyrin is classified as diterpene.

Explanation of Solution

The structure of isoprene is,

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  15

Figure 1

The isoprene unit contains four carbon atoms in the long chain and one carbon atom in branch. Isoprene unit in a terpene consists of carbon-carbon sigma or pi bonds.

The isoprene units in the given compound are shown below.

Organic Chemistry, Chapter 31, Problem 31.27P , additional homework tip  16

Figure 9

The highlighted bonds represent the isoprene unit. There are four isoprene units present in the given compound. The β-amyrin is classified as diterpene.

Conclusion

The β-amyrin is classified as diterpene.

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