(a) Interpretation: The molecular structure is to be drawn for the given name. Concept introduction: E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond. In cyclic compounds with less than eight atoms, a ring double bond can have only one configuration, with the ring continuing on the same side of the double bond. The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Question

Complete the following reactions, clearly indicating regio-and stereochemistry where applicable. In cases, where ortho-and para-products are formed, draw both.

Answer 1

Question

Chapter C, Problem C.36P

Interpretation Introduction

(a)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

In cyclic compounds with less than eight atoms, a ring double bond can have only one configuration, with the ring continuing on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(b)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(c)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(d)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

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Answer 2

Question

Chapter C, Problem C.36P

Interpretation Introduction

(a)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

In cyclic compounds with less than eight atoms, a ring double bond can have only one configuration, with the ring continuing on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(b)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(c)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(d)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

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Answer 3

Question

Chapter C, Problem C.36P

Interpretation Introduction

(a)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

In cyclic compounds with less than eight atoms, a ring double bond can have only one configuration, with the ring continuing on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(b)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(c)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(d)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

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Answer 4

Question

Chapter C, Problem C.36P

Interpretation Introduction

(a)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

In cyclic compounds with less than eight atoms, a ring double bond can have only one configuration, with the ring continuing on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(b)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(c)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(d)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

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Answer 5

Chapter C, Problem C.36P

Interpretation Introduction

(a)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

In cyclic compounds with less than eight atoms, a ring double bond can have only one configuration, with the ring continuing on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(b)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(c)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Interpretation Introduction

(d)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Answer 6

Chapter C, Problem C.36P

Interpretation Introduction

(a)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

In cyclic compounds with less than eight atoms, a ring double bond can have only one configuration, with the ring continuing on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Answer 7

Chapter C, Problem C.36P

Interpretation Introduction

(a)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

In cyclic compounds with less than eight atoms, a ring double bond can have only one configuration, with the ring continuing on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The molecular structure is to be drawn for the given name.

Concept introduction:

E/Z designations indicate the absolute stereochemistry of double bonds. An E designation indicates the higher priority groups on the double bond are on opposite sides of the bond. A Z designation indicates that they are on the same side of the double bond.

The groups at each end of the double bond are assigned priorities on the basis of Cahn-Ingold-Prelog rules.

Answer 14

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Answer 25

Ch. C - Prob. C.1P Ch. C - Prob. C.2P Ch. C - Prob. C.3P Ch. C - Prob. C.4P Ch. C - Prob. C.5P Ch. C - Prob. C.6P Ch. C - Prob. C.7P Ch. C - Prob. C.8P Ch. C - Prob. C.9P Ch. C - Prob. C.10P

Solution Summary: The author explains the structure of (Z)-3-phenylhex-2-ene.

Chapter C Solutions