(a) Interpretation: The four stereogenic centers in sorbitol are to be labeled as R or S . Concept introduction: The stereogenic centers with R , S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

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Answer 1

Question

Chapter 5.9, Problem 27P

Interpretation Introduction

(a)

Interpretation: The four stereogenic centers in sorbitol are to be labeled as R or S.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(b)

Interpretation: The relation between sorbitol and A is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The relation between sorbitol and B is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

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(a) Locate the stereogenic centers in the ball-and-stick model of lisinopril, a drug used to treat high blood pressure. (b) Label each stereogenic center as R or S.

(a) Locate the stereogenic centers in the ball-and-stick model of ezetimibe (trade name Zetia), a cholesterol-lowering drug. (b) Label each stereogenic center as R or S.

Eleostearic acid is an unsaturated fatty acid obtained from the seeds of the tung oil tree (Aleurites fordii), a deciduous tree native to China. (a) Draw the structure of a stereoisomer that has a higher melting point than eleostearic acid. (b) Draw the structure of a stereoisomer that has a lower melting point.

Answer 2

Question

Chapter 5.9, Problem 27P

Interpretation Introduction

(a)

Interpretation: The four stereogenic centers in sorbitol are to be labeled as R or S.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(b)

Interpretation: The relation between sorbitol and A is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The relation between sorbitol and B is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

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Answer 3

Question

Chapter 5.9, Problem 27P

Interpretation Introduction

(a)

Interpretation: The four stereogenic centers in sorbitol are to be labeled as R or S.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(b)

Interpretation: The relation between sorbitol and A is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The relation between sorbitol and B is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

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Answer 4

Question

Chapter 5.9, Problem 27P

Interpretation Introduction

(a)

Interpretation: The four stereogenic centers in sorbitol are to be labeled as R or S.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(b)

Interpretation: The relation between sorbitol and A is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The relation between sorbitol and B is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

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Answer 5

Chapter 5.9, Problem 27P

Interpretation Introduction

(a)

Interpretation: The four stereogenic centers in sorbitol are to be labeled as R or S.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Interpretation Introduction

(b)

Interpretation: The relation between sorbitol and A is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The relation between sorbitol and B is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer 6

Chapter 5.9, Problem 27P

Interpretation Introduction

(a)

Interpretation: The four stereogenic centers in sorbitol are to be labeled as R or S.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Answer 7

Chapter 5.9, Problem 27P

Interpretation Introduction

(a)

Interpretation: The four stereogenic centers in sorbitol are to be labeled as R or S.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. On moving from higher priority to lower priority substituent in clockwise direction, the compound is assigned with R configuration. On moving from higher priority to lower priority substituent in anticlockwise direction, the compound is assigned with S configuration.

Answer 8

Interpretation Introduction

(b)

Interpretation: The relation between sorbitol and A is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer 9

Interpretation Introduction

(b)

Interpretation: The relation between sorbitol and A is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer 10

Interpretation Introduction

(c)

Interpretation: The relation between sorbitol and B is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer 11

Interpretation Introduction

(c)

Interpretation: The relation between sorbitol and B is to be stated.

Concept introduction: The stereogenic centers with R,S configuration are assigned according to Cahn-Ingold-Prelog rules. According to these rules, the substituents attached to stereogenic centers are given priority. R,S configuration can be used to determine the relation between two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer 12

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Answer 13

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Answer 14

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Answer 15

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...

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