For ( − )-nicotine, ( − )-adrenaline, and ( − )-thyroxine , appropriate R, S symbols are to be assigned. Concept introduction: When a tetrahedral carbon atom is connected to four different atoms or groups, then that carbon is called a chiral carbon or chiral center. The absolute configuration is the three dimensional spatial arrangement of substituents attached to a chiral center. The Cahn-Ingold-Prelog rule system lists the substituents bonded to the chiral center in the order of decreasing atomic number. A higher atomic number has a higher priority over a lower atomic number for the substituent. When there are two identical atoms directly attached to the chirality center, then they are ranked on the basis of the atomic numbers of the other atoms attached to them. If an atom has multiple bonds, it is considered to be replicated as a substituent on that atom. If isotopes are present, they are ranked on the basis of their atomic masses. The molecule is oriented such that the lowest ranked group points away from the observer. If the remaining three groups in order of decreasing priority trace a clockwise path, the configuration is R. If the remaining three groups in order of decreasing priority trace a counter clockwise path, the configuration is S.

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Answer 1

Question

Chapter 4.8, Problem 12P

Interpretation Introduction

Interpretation:

For (−)-nicotine, (−)-adrenaline, and (−)-thyroxine, appropriate R, S symbols are to be assigned.

Concept introduction:

When a tetrahedral carbon atom is connected to four different atoms or groups, then that carbon is called a chiral carbon or chiral center.

The absolute configuration is the three dimensional spatial arrangement of substituents attached to a chiral center.

The Cahn-Ingold-Prelog rule system lists the substituents bonded to the chiral center in the order of decreasing atomic number. A higher atomic number has a higher priority over a lower atomic number for the substituent.

When there are two identical atoms directly attached to the chirality center, then they are ranked on the basis of the atomic numbers of the other atoms attached to them.

If an atom has multiple bonds, it is considered to be replicated as a substituent on that atom.

If isotopes are present, they are ranked on the basis of their atomic masses.

The molecule is oriented such that the lowest ranked group points away from the observer.

If the remaining three groups in order of decreasing priority trace a clockwise path, the configuration is R.

If the remaining three groups in order of decreasing priority trace a counter clockwise path, the configuration is S.

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Answer 2

Question

Chapter 4.8, Problem 12P

Interpretation Introduction

Interpretation:

For (−)-nicotine, (−)-adrenaline, and (−)-thyroxine, appropriate R, S symbols are to be assigned.

Concept introduction:

When a tetrahedral carbon atom is connected to four different atoms or groups, then that carbon is called a chiral carbon or chiral center.

The absolute configuration is the three dimensional spatial arrangement of substituents attached to a chiral center.

The Cahn-Ingold-Prelog rule system lists the substituents bonded to the chiral center in the order of decreasing atomic number. A higher atomic number has a higher priority over a lower atomic number for the substituent.

When there are two identical atoms directly attached to the chirality center, then they are ranked on the basis of the atomic numbers of the other atoms attached to them.

If an atom has multiple bonds, it is considered to be replicated as a substituent on that atom.

If isotopes are present, they are ranked on the basis of their atomic masses.

The molecule is oriented such that the lowest ranked group points away from the observer.

If the remaining three groups in order of decreasing priority trace a clockwise path, the configuration is R.

If the remaining three groups in order of decreasing priority trace a counter clockwise path, the configuration is S.

Expert Solution & Answer

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Answer 3

Question

Chapter 4.8, Problem 12P

Interpretation Introduction

Interpretation:

For (−)-nicotine, (−)-adrenaline, and (−)-thyroxine, appropriate R, S symbols are to be assigned.

Concept introduction:

When a tetrahedral carbon atom is connected to four different atoms or groups, then that carbon is called a chiral carbon or chiral center.

The absolute configuration is the three dimensional spatial arrangement of substituents attached to a chiral center.

The Cahn-Ingold-Prelog rule system lists the substituents bonded to the chiral center in the order of decreasing atomic number. A higher atomic number has a higher priority over a lower atomic number for the substituent.

When there are two identical atoms directly attached to the chirality center, then they are ranked on the basis of the atomic numbers of the other atoms attached to them.

If an atom has multiple bonds, it is considered to be replicated as a substituent on that atom.

If isotopes are present, they are ranked on the basis of their atomic masses.

The molecule is oriented such that the lowest ranked group points away from the observer.

If the remaining three groups in order of decreasing priority trace a clockwise path, the configuration is R.

If the remaining three groups in order of decreasing priority trace a counter clockwise path, the configuration is S.

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Answer 4

Question

Chapter 4.8, Problem 12P

Interpretation Introduction

Interpretation:

For (−)-nicotine, (−)-adrenaline, and (−)-thyroxine, appropriate R, S symbols are to be assigned.

Concept introduction:

When a tetrahedral carbon atom is connected to four different atoms or groups, then that carbon is called a chiral carbon or chiral center.

The absolute configuration is the three dimensional spatial arrangement of substituents attached to a chiral center.

The Cahn-Ingold-Prelog rule system lists the substituents bonded to the chiral center in the order of decreasing atomic number. A higher atomic number has a higher priority over a lower atomic number for the substituent.

When there are two identical atoms directly attached to the chirality center, then they are ranked on the basis of the atomic numbers of the other atoms attached to them.

If an atom has multiple bonds, it is considered to be replicated as a substituent on that atom.

If isotopes are present, they are ranked on the basis of their atomic masses.

The molecule is oriented such that the lowest ranked group points away from the observer.

If the remaining three groups in order of decreasing priority trace a clockwise path, the configuration is R.

If the remaining three groups in order of decreasing priority trace a counter clockwise path, the configuration is S.

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Answer 5

Chapter 4.8, Problem 12P

Interpretation Introduction

Interpretation:

For (−)-nicotine, (−)-adrenaline, and (−)-thyroxine, appropriate R, S symbols are to be assigned.

Concept introduction:

When a tetrahedral carbon atom is connected to four different atoms or groups, then that carbon is called a chiral carbon or chiral center.

The absolute configuration is the three dimensional spatial arrangement of substituents attached to a chiral center.

The Cahn-Ingold-Prelog rule system lists the substituents bonded to the chiral center in the order of decreasing atomic number. A higher atomic number has a higher priority over a lower atomic number for the substituent.

When there are two identical atoms directly attached to the chirality center, then they are ranked on the basis of the atomic numbers of the other atoms attached to them.

If an atom has multiple bonds, it is considered to be replicated as a substituent on that atom.

If isotopes are present, they are ranked on the basis of their atomic masses.

The molecule is oriented such that the lowest ranked group points away from the observer.

If the remaining three groups in order of decreasing priority trace a clockwise path, the configuration is R.

If the remaining three groups in order of decreasing priority trace a counter clockwise path, the configuration is S.

Answer 6

Chapter 4.8, Problem 12P

Interpretation Introduction

Interpretation:

For (−)-nicotine, (−)-adrenaline, and (−)-thyroxine, appropriate R, S symbols are to be assigned.

Concept introduction:

When a tetrahedral carbon atom is connected to four different atoms or groups, then that carbon is called a chiral carbon or chiral center.

The absolute configuration is the three dimensional spatial arrangement of substituents attached to a chiral center.

The Cahn-Ingold-Prelog rule system lists the substituents bonded to the chiral center in the order of decreasing atomic number. A higher atomic number has a higher priority over a lower atomic number for the substituent.

When there are two identical atoms directly attached to the chirality center, then they are ranked on the basis of the atomic numbers of the other atoms attached to them.

If an atom has multiple bonds, it is considered to be replicated as a substituent on that atom.

If isotopes are present, they are ranked on the basis of their atomic masses.

The molecule is oriented such that the lowest ranked group points away from the observer.

If the remaining three groups in order of decreasing priority trace a clockwise path, the configuration is R.

If the remaining three groups in order of decreasing priority trace a counter clockwise path, the configuration is S.

Answer 7

Chapter 4.8, Problem 12P

Interpretation Introduction

Interpretation:

For (−)-nicotine, (−)-adrenaline, and (−)-thyroxine, appropriate R, S symbols are to be assigned.

Concept introduction:

When a tetrahedral carbon atom is connected to four different atoms or groups, then that carbon is called a chiral carbon or chiral center.

The absolute configuration is the three dimensional spatial arrangement of substituents attached to a chiral center.

The Cahn-Ingold-Prelog rule system lists the substituents bonded to the chiral center in the order of decreasing atomic number. A higher atomic number has a higher priority over a lower atomic number for the substituent.

When there are two identical atoms directly attached to the chirality center, then they are ranked on the basis of the atomic numbers of the other atoms attached to them.

If an atom has multiple bonds, it is considered to be replicated as a substituent on that atom.

If isotopes are present, they are ranked on the basis of their atomic masses.

The molecule is oriented such that the lowest ranked group points away from the observer.

If the remaining three groups in order of decreasing priority trace a clockwise path, the configuration is R.

If the remaining three groups in order of decreasing priority trace a counter clockwise path, the configuration is S.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 4.2 - Examine the following for chirality centers:Ch. 4.2 - Prob. 2P Ch. 4.3 - Prob. 3P Ch. 4.3 - Prob. 4P Ch. 4.4 - Prob. 5P Ch. 4.4 - Prob. 6P Ch. 4.5 - Does the molecular model shown represent...Ch. 4.6 - Assign absolute configurations as R or S to each...Ch. 4.6 - Draw three-dimensional representations of Ch. 4.7 - Prob. 10P

Solution Summary: The author explains how the Cahn-Ingold-Prelog rule system lists the substituents attached to the chiral center in the order of decreasing atomic number.

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