(a) Interpretation: The enantiomers ( R and S ) for the given biologically active compound are to be drawn. Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers. The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R -stereoisomer, and if this is counter-clockwise, then it is the S -stereoisomer. R and S -stereoisomer are mirror images of each other.

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Answer 1

Question

Chapter 5, Problem 47P

Interpretation Introduction

(a)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Interpretation Introduction

(b)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

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Locate the stereogenic centers in each compound. A molecule may have one or more stereogenic centers. Gabapentin enacarbil [part (d)] is used to treat seizures and certain types of chronic pain.

Saquinavir (trade name Invirase) is a protease inhibitor, used to treat HIV (human immunodeficiency virus). a.Locate all stereogenic centers in saquinavir, and label each stereogenic center as R or S. b.Draw the enantiomer of saquinavir. c.Draw a diastereomer of saquinavir. d.Draw a constitutional isomer that contains at least one different functional group.

Draw both enantiomers of clopidogrel (trade name Plavix), a drug given to prevent the formation of blood clots in persons who have a history of stroke or coronary artery disease. Plavix is sold as a single enantiomer with the S configuration. Which enantiomer is Plavix?

Answer 2

Question

Chapter 5, Problem 47P

Interpretation Introduction

(a)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Interpretation Introduction

(b)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

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Answer 3

Question

Chapter 5, Problem 47P

Interpretation Introduction

(a)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Interpretation Introduction

(b)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

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Answer 4

Question

Chapter 5, Problem 47P

Interpretation Introduction

(a)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Interpretation Introduction

(b)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

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Answer 5

Chapter 5, Problem 47P

Interpretation Introduction

(a)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Interpretation Introduction

(b)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Answer 6

Chapter 5, Problem 47P

Interpretation Introduction

(a)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Answer 7

Chapter 5, Problem 47P

Interpretation Introduction

(a)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Answer 8

Interpretation Introduction

(b)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Answer 9

Interpretation Introduction

(b)

Interpretation: The enantiomers (R and S) for the given biologically active compound are to be drawn.

Concept introduction: Enantiomers of a compound are the stereoisomers which are non-super imposable mirror images. A carbon atom bonded to four different groups is known as a chiral carbon. A compound which has a chiral carbon can be resolved into enantiomers.

The naming of chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules. If the priority assigned to each group attached to the chirality center in a molecule is in a clockwise direction, then it is the R-stereoisomer, and if this is counter-clockwise, then it is the S-stereoisomer. R and S-stereoisomer are mirror images of each other.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 5.1 - Prob. 1P Ch. 5.2 - Prob. 2P Ch. 5.3 - Draw the mirror image of each compound. Label each...Ch. 5.3 - Prob. 4P Ch. 5.3 - A molecule is achiral if it has a plane of...Ch. 5.6 - Prob. 17P Ch. 5.6 - Prob. 18P Ch. 5.7 - Prob. 19P Ch. 5.7 - Prob. 20P Ch. 5.7 - Problem 5.18 Compounds E and F are two isomers of...

Solution Summary: The author explains that enantiomers of a compound are non-superimposable mirror images, based on Cahn-Ingold-Prelog priority rules.

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