The complete IUPAC name of indicated enantiomer should be written as well as numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl 2 with S-1,3-dichloropentane at C3 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter. Concept introduction: Halogenation products are governed by the achirality or already present stereocenter in the molecule. If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive. If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

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Answer 1

Question

Chapter 5, Problem 57P

(a)

Interpretation Introduction

Interpretation:The complete IUPAC name of indicated enantiomer should be written as well as numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C3 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction: Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C4 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at at C5 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

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Answer 2

Question

Chapter 5, Problem 57P

(a)

Interpretation Introduction

Interpretation:The complete IUPAC name of indicated enantiomer should be written as well as numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C3 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction: Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C4 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at at C5 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

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Answer 3

Question

Chapter 5, Problem 57P

(a)

Interpretation Introduction

Interpretation:The complete IUPAC name of indicated enantiomer should be written as well as numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C3 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction: Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C4 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at at C5 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

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Answer 4

Question

Chapter 5, Problem 57P

(a)

Interpretation Introduction

Interpretation:The complete IUPAC name of indicated enantiomer should be written as well as numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C3 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction: Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C4 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at at C5 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

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Answer 5

Chapter 5, Problem 57P

(a)

Interpretation Introduction

Interpretation:The complete IUPAC name of indicated enantiomer should be written as well as numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C3 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction: Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C4 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

(c)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at at C5 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 6

Chapter 5, Problem 57P

(a)

Interpretation Introduction

Interpretation:The complete IUPAC name of indicated enantiomer should be written as well as numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C3 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction: Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 7

Chapter 5, Problem 57P

(a)

Interpretation Introduction

Interpretation:The complete IUPAC name of indicated enantiomer should be written as well as numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C3 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction: Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 8

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C4 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 9

(b)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at C4 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at the stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 10

(c)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at at C5 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 11

(c)

Interpretation Introduction

Interpretation: Numbers of possible stereoisomeric products formed in the chlorination with 1 mol Cl2 with S-1,3-dichloropentane at at C5 should be determined and whether they are formed in equal or unequal amounts should be indicated along with S and R designation at stereocenter.

Concept introduction:Halogenation products are governed by the achirality or already present stereocenter in the molecule.

If the halogenation occurs at the chiral center of the substrate it results in a racemic mixture. This is attributed to formation of achiral radical intermediate that can be attacked equally from the top face or bottom face. Thus two enantiomers R and S are formed in equal amount that makes the overall mixture optically inactive.

If the halogenation occurs at one of the two chiral centers of the substrate it results in change in absolute configuration at only one of the stereocenter and thus diastereoisomer result. These diastereomers are formed in unequal amounts.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 5.1 - Prob. 5.3E Ch. 5.1 - Prob. 5.4E Ch. 5.1 - Prob. 5.5E Ch. 5.2 - Prob. 5.6E Ch. 5.2 - Prob. 5.8TIY Ch. 5.3 - Prob. 5.9E Ch. 5.3 - Prob. 5.11TIY Ch. 5.3 - Prob. 5.12E Ch. 5.4 - Prob. 5.13E Ch. 5.4 - Prob. 5.14E

Solution Summary: The author explains that halogenation products are governed by achirality or already present stereocenter in the molecule.

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