(a) Interpretation: A diene that would react with Grubbs catalyst to produce the given compound is to be drawn. Concept introduction: An alkene metathesis occurs when one or more alkenes are treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called ring-closing metathesis. A ring is formed in the reaction; therefore, two C=C terminal groups in the reactant must be on the same molecule.

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Answer 1

Question

Chapter 19, Problem 19.63P

Interpretation Introduction

(a)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes are treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called ring-closing metathesis. A ring is formed in the reaction; therefore, two C=C terminal groups in the reactant must be on the same molecule.

Interpretation Introduction

(b)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes is treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called a ring-closing metathesis. A ring is formed in the reaction, therefore, two C=C terminal groups in the reactant must be on the same molecule.

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1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)

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+

Answer 2

Question

Chapter 19, Problem 19.63P

Interpretation Introduction

(a)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes are treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called ring-closing metathesis. A ring is formed in the reaction; therefore, two C=C terminal groups in the reactant must be on the same molecule.

Interpretation Introduction

(b)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes is treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called a ring-closing metathesis. A ring is formed in the reaction, therefore, two C=C terminal groups in the reactant must be on the same molecule.

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Answer 3

Question

Chapter 19, Problem 19.63P

Interpretation Introduction

(a)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes are treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called ring-closing metathesis. A ring is formed in the reaction; therefore, two C=C terminal groups in the reactant must be on the same molecule.

Interpretation Introduction

(b)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes is treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called a ring-closing metathesis. A ring is formed in the reaction, therefore, two C=C terminal groups in the reactant must be on the same molecule.

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Answer 4

Question

Chapter 19, Problem 19.63P

Interpretation Introduction

(a)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes are treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called ring-closing metathesis. A ring is formed in the reaction; therefore, two C=C terminal groups in the reactant must be on the same molecule.

Interpretation Introduction

(b)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes is treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called a ring-closing metathesis. A ring is formed in the reaction, therefore, two C=C terminal groups in the reactant must be on the same molecule.

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Answer 5

Chapter 19, Problem 19.63P

Interpretation Introduction

(a)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes are treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called ring-closing metathesis. A ring is formed in the reaction; therefore, two C=C terminal groups in the reactant must be on the same molecule.

Interpretation Introduction

(b)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes is treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called a ring-closing metathesis. A ring is formed in the reaction, therefore, two C=C terminal groups in the reactant must be on the same molecule.

Answer 6

Chapter 19, Problem 19.63P

Interpretation Introduction

(a)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes are treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called ring-closing metathesis. A ring is formed in the reaction; therefore, two C=C terminal groups in the reactant must be on the same molecule.

Answer 7

Chapter 19, Problem 19.63P

Interpretation Introduction

(a)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes are treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called ring-closing metathesis. A ring is formed in the reaction; therefore, two C=C terminal groups in the reactant must be on the same molecule.

Answer 8

Interpretation Introduction

(b)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes is treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called a ring-closing metathesis. A ring is formed in the reaction, therefore, two C=C terminal groups in the reactant must be on the same molecule.

Answer 9

Interpretation Introduction

(b)

Interpretation:

A diene that would react with Grubbs catalyst to produce the given compound is to be drawn.

Concept introduction:

An alkene metathesis occurs when one or more alkenes is treated with Grubbs catalyst, which contains a Ru=C bond. In the product of an alkene metathesis, the fragments that are joined by a double bond were initially part of a double bond to other fragments in the reactant. These reactions are particularly useful when the reactants are terminal alkenes. When the reaction produces a new ring, it is called a ring-closing metathesis. A ring is formed in the reaction, therefore, two C=C terminal groups in the reactant must be on the same molecule.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 19 - Prob. 19.1P Ch. 19 - Prob. 19.2P Ch. 19 - Prob. 19.3P Ch. 19 - Prob. 19.4P Ch. 19 - Prob. 19.5P Ch. 19 - Prob. 19.6P Ch. 19 - Prob. 19.7P Ch. 19 - Prob. 19.8P Ch. 19 - Prob. 19.9P Ch. 19 - Prob. 19.10P

Solution Summary: The author explains how a diene reacts with Grubbs catalyst to produce the given compound by undoing alkene metathesis.

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Chapter 19 Solutions