(a) Interpretation: The relation between given pair of compounds is to be determined. 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. Enantiomer of a compound has opposite configuration at stereogenic centers. 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 1

Question

Chapter 5, Problem 5.64P

Interpretation Introduction

(a)

Interpretation: The relation between given pair of compounds is to be determined.

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.

Enantiomer of a compound has opposite configuration at stereogenic centers. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(b)

Interpretation: Each compound is to be labeled as chiral or achiral.

Concept introduction: An atom containing four different atoms or groups, which produce stereoisomers on exchange of any two groups. These centers are known as stereogenic centers.

Interpretation Introduction

(c)

Interpretation: Among the given compounds, optically active compounds are to be determined.

Concept introduction: The phenomenon by which a chiral molecule is observed to rotate the plane polarized light in either a clockwise direction or anticlockwise direction is called as optical activity of the molecule.

Interpretation Introduction

(d)

Interpretation: Among the given compounds, compounds which have plane of symmetry are to be determined.

Concept introduction: An imaginary plane which bisects the molecule into halves such that these halves are mirror images of each other. This is known as plane of symmetry.

Interpretation Introduction

(e)

Interpretation: Among the given pair of compounds, boiling points is to be compared.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

Interpretation Introduction

(g)

Interpretation: Equal mixtures of compounds C and D and compounds B and C is optically active or not is to be predicted.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

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19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

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Q4: Write organic product(s) of the following reactions and show the curved-arrow mechanism of the reactions. Br MeOH OSO2CH3 MeOH

Answer 2

Question

Chapter 5, Problem 5.64P

Interpretation Introduction

(a)

Interpretation: The relation between given pair of compounds is to be determined.

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.

Enantiomer of a compound has opposite configuration at stereogenic centers. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(b)

Interpretation: Each compound is to be labeled as chiral or achiral.

Concept introduction: An atom containing four different atoms or groups, which produce stereoisomers on exchange of any two groups. These centers are known as stereogenic centers.

Interpretation Introduction

(c)

Interpretation: Among the given compounds, optically active compounds are to be determined.

Concept introduction: The phenomenon by which a chiral molecule is observed to rotate the plane polarized light in either a clockwise direction or anticlockwise direction is called as optical activity of the molecule.

Interpretation Introduction

(d)

Interpretation: Among the given compounds, compounds which have plane of symmetry are to be determined.

Concept introduction: An imaginary plane which bisects the molecule into halves such that these halves are mirror images of each other. This is known as plane of symmetry.

Interpretation Introduction

(e)

Interpretation: Among the given pair of compounds, boiling points is to be compared.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

Interpretation Introduction

(g)

Interpretation: Equal mixtures of compounds C and D and compounds B and C is optically active or not is to be predicted.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

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Answer 3

Question

Chapter 5, Problem 5.64P

Interpretation Introduction

(a)

Interpretation: The relation between given pair of compounds is to be determined.

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.

Enantiomer of a compound has opposite configuration at stereogenic centers. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(b)

Interpretation: Each compound is to be labeled as chiral or achiral.

Concept introduction: An atom containing four different atoms or groups, which produce stereoisomers on exchange of any two groups. These centers are known as stereogenic centers.

Interpretation Introduction

(c)

Interpretation: Among the given compounds, optically active compounds are to be determined.

Concept introduction: The phenomenon by which a chiral molecule is observed to rotate the plane polarized light in either a clockwise direction or anticlockwise direction is called as optical activity of the molecule.

Interpretation Introduction

(d)

Interpretation: Among the given compounds, compounds which have plane of symmetry are to be determined.

Concept introduction: An imaginary plane which bisects the molecule into halves such that these halves are mirror images of each other. This is known as plane of symmetry.

Interpretation Introduction

(e)

Interpretation: Among the given pair of compounds, boiling points is to be compared.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

Interpretation Introduction

(g)

Interpretation: Equal mixtures of compounds C and D and compounds B and C is optically active or not is to be predicted.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

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Answer 4

Question

Chapter 5, Problem 5.64P

Interpretation Introduction

(a)

Interpretation: The relation between given pair of compounds is to be determined.

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.

Enantiomer of a compound has opposite configuration at stereogenic centers. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(b)

Interpretation: Each compound is to be labeled as chiral or achiral.

Concept introduction: An atom containing four different atoms or groups, which produce stereoisomers on exchange of any two groups. These centers are known as stereogenic centers.

Interpretation Introduction

(c)

Interpretation: Among the given compounds, optically active compounds are to be determined.

Concept introduction: The phenomenon by which a chiral molecule is observed to rotate the plane polarized light in either a clockwise direction or anticlockwise direction is called as optical activity of the molecule.

Interpretation Introduction

(d)

Interpretation: Among the given compounds, compounds which have plane of symmetry are to be determined.

Concept introduction: An imaginary plane which bisects the molecule into halves such that these halves are mirror images of each other. This is known as plane of symmetry.

Interpretation Introduction

(e)

Interpretation: Among the given pair of compounds, boiling points is to be compared.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

Interpretation Introduction

(g)

Interpretation: Equal mixtures of compounds C and D and compounds B and C is optically active or not is to be predicted.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

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Answer 5

Chapter 5, Problem 5.64P

Interpretation Introduction

(a)

Interpretation: The relation between given pair of compounds is to be determined.

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.

Enantiomer of a compound has opposite configuration at stereogenic centers. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(b)

Interpretation: Each compound is to be labeled as chiral or achiral.

Concept introduction: An atom containing four different atoms or groups, which produce stereoisomers on exchange of any two groups. These centers are known as stereogenic centers.

Interpretation Introduction

(c)

Interpretation: Among the given compounds, optically active compounds are to be determined.

Concept introduction: The phenomenon by which a chiral molecule is observed to rotate the plane polarized light in either a clockwise direction or anticlockwise direction is called as optical activity of the molecule.

Interpretation Introduction

(d)

Interpretation: Among the given compounds, compounds which have plane of symmetry are to be determined.

Concept introduction: An imaginary plane which bisects the molecule into halves such that these halves are mirror images of each other. This is known as plane of symmetry.

Interpretation Introduction

(e)

Interpretation: Among the given pair of compounds, boiling points is to be compared.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

Interpretation Introduction

(g)

Interpretation: Equal mixtures of compounds C and D and compounds B and C is optically active or not is to be predicted.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

Answer 6

Chapter 5, Problem 5.64P

Interpretation Introduction

(a)

Interpretation: The relation between given pair of compounds is to be determined.

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.

Enantiomer of a compound has opposite configuration at stereogenic centers. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer 7

Chapter 5, Problem 5.64P

Interpretation Introduction

(a)

Interpretation: The relation between given pair of compounds is to be determined.

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.

Enantiomer of a compound has opposite configuration at stereogenic centers. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer 8

Interpretation Introduction

(b)

Interpretation: Each compound is to be labeled as chiral or achiral.

Concept introduction: An atom containing four different atoms or groups, which produce stereoisomers on exchange of any two groups. These centers are known as stereogenic centers.

Answer 9

Interpretation Introduction

(b)

Interpretation: Each compound is to be labeled as chiral or achiral.

Concept introduction: An atom containing four different atoms or groups, which produce stereoisomers on exchange of any two groups. These centers are known as stereogenic centers.

Answer 10

Interpretation Introduction

(c)

Interpretation: Among the given compounds, optically active compounds are to be determined.

Concept introduction: The phenomenon by which a chiral molecule is observed to rotate the plane polarized light in either a clockwise direction or anticlockwise direction is called as optical activity of the molecule.

Answer 11

Interpretation Introduction

(c)

Interpretation: Among the given compounds, optically active compounds are to be determined.

Concept introduction: The phenomenon by which a chiral molecule is observed to rotate the plane polarized light in either a clockwise direction or anticlockwise direction is called as optical activity of the molecule.

Answer 12

Interpretation Introduction

(d)

Interpretation: Among the given compounds, compounds which have plane of symmetry are to be determined.

Concept introduction: An imaginary plane which bisects the molecule into halves such that these halves are mirror images of each other. This is known as plane of symmetry.

Answer 13

Interpretation Introduction

(d)

Interpretation: Among the given compounds, compounds which have plane of symmetry are to be determined.

Concept introduction: An imaginary plane which bisects the molecule into halves such that these halves are mirror images of each other. This is known as plane of symmetry.

Answer 14

Interpretation Introduction

(e)

Interpretation: Among the given pair of compounds, boiling points is to be compared.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

Answer 15

Interpretation Introduction

(e)

Interpretation: Among the given pair of compounds, boiling points is to be compared.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

Answer 16

Interpretation Introduction

(g)

Interpretation: Equal mixtures of compounds C and D and compounds B and C is optically active or not is to be predicted.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

Answer 17

Interpretation Introduction

(g)

Interpretation: Equal mixtures of compounds C and D and compounds B and C is optically active or not is to be predicted.

Concept introduction: Enantiomers are stereoisomers, which are non-superimposable images of each other. They have identical physical and chemical properties in symmetric environment. They rotate the plane-polarized light in equal amounts and in opposite directions.

Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration. Diastereomers of compound do not have mirror image relationship. They have different physical and chemical properties.

Answer 18

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Answer 19

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Answer 20

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Answer 21

Ch. 5 - Prob. 5.1P Ch. 5 - Prob. 5.2P Ch. 5 - Draw the mirror image of each compound. Label each...Ch. 5 - Prob. 5.4P Ch. 5 - A molecule is achiral if it has a plane of...Ch. 5 - Problem 5.6 Locate the stereogenic centers in each...Ch. 5 - The facts in section 5.4A can be used to locate...Ch. 5 - Prob. 5.8P Ch. 5 - Prob. 5.9P Ch. 5 - Prob. 5.10P

Solution Summary: The author explains that the relationship between compounds A and B is constitutional isomers, and compounds B and C is diastereomer.

Concept explainers

(b)

Interpretation: Each compound is to be labeled as chiral or achiral.

Concept introduction: An atom containing four different atoms or groups, which produce stereoisomers on exchange of any two groups. These centers are known as stereogenic centers.

(d)

Interpretation: Among the given compounds, compounds which have plane of symmetry are to be determined.

Concept introduction: An imaginary plane which bisects the molecule into halves such that these halves are mirror images of each other. This is known as plane of symmetry.

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Chapter 5 Solutions

Solution Summary: The author explains that the relationship between compounds A and B is constitutional isomers, and compounds B and C is diastereomer.

Concept explainers

(b) Interpretation: Each compound is to be labeled as chiral or achiral. Concept introduction: An atom containing four different atoms or groups, which produce stereoisomers on exchange of any two groups. These centers are known as stereogenic centers.

(d) Interpretation: Among the given compounds, compounds which have plane of symmetry are to be determined. Concept introduction: An imaginary plane which bisects the molecule into halves such that these halves are mirror images of each other. This is known as plane of symmetry.

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Chapter 5 Solutions

(b)

Interpretation: Each compound is to be labeled as chiral or achiral.

Concept introduction: An atom containing four different atoms or groups, which produce stereoisomers on exchange of any two groups. These centers are known as stereogenic centers.

(d)

Interpretation: Among the given compounds, compounds which have plane of symmetry are to be determined.

Concept introduction: An imaginary plane which bisects the molecule into halves such that these halves are mirror images of each other. This is known as plane of symmetry.