(a) Interpretation: The structure of the e n d o − dicyclopentadiene is to be drawn. Concept introduction: A chemical reaction that involves [ 4 + 2 ] cycloaddition is known as Diels-Alder reaction. The reactant molecules that give rise to the product are diene and dienophile. The rate of reaction is fast when the electronegative group is attached to dienophile. In this type of reaction, syn addition takes place.

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Answer 1

Question

Chapter 18, Problem 18.72AP

Interpretation Introduction

(a)

Interpretation:

The structure of the endo−dicyclopentadiene is to be drawn.

Concept introduction:

A chemical reaction that involves [4+2] cycloaddition is known as Diels-Alder reaction. The reactant molecules that give rise to the product are diene and dienophile. The rate of reaction is fast when the electronegative group is attached to dienophile. In this type of reaction, syn addition takes place.

Interpretation Introduction

(b)

Interpretation:

The structure of the polymer formed when endo−dicyclopentadiene is subjected to ROMP is to be drawn. The reason as to why the polymer formed is strong is to be stated.

Concept introduction:

The process by which respective monomers combine to form polymers is known as polymerization. ROMP (ring-opening metathesis polymerization) is a chain-growth polymerization in which ring-opening takes place due to strain. It is also known as olefin-metathesis.

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1)Chemistry students are taking an experimental course in organic chemistry at a public university. During an experiment involving conjugated dienes, some doubts arose when discussing the results obtained so far: (a) A student obtained two products from the reaction of 1,3-cyclohexadiene with Br2. His lab partner was surprised to get only one product from the reaction of 1,3 - cyclohexadiene with HBr. Explain these distinct results. (b) One student, seeing the discussion of colleagues, commented that she obtained two distinct products when reacting 1,3,5-hexatriene with HBr, with different yields just by changing the reaction temperature. Explain the results she obtained using reaction mechanism and based on kinetic and thermodynamic control involving conjugated dienes.

Give reasons: (i) C—Cl bond length in chlorobenzene is shorter than C—Cl bond length in CH3—Cl.(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(iii) SN1 reactions are accompanied by racemization in optically active alkyl halides

The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formulaC5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.

Answer 2

Question

Chapter 18, Problem 18.72AP

Interpretation Introduction

(a)

Interpretation:

The structure of the endo−dicyclopentadiene is to be drawn.

Concept introduction:

A chemical reaction that involves [4+2] cycloaddition is known as Diels-Alder reaction. The reactant molecules that give rise to the product are diene and dienophile. The rate of reaction is fast when the electronegative group is attached to dienophile. In this type of reaction, syn addition takes place.

Interpretation Introduction

(b)

Interpretation:

The structure of the polymer formed when endo−dicyclopentadiene is subjected to ROMP is to be drawn. The reason as to why the polymer formed is strong is to be stated.

Concept introduction:

The process by which respective monomers combine to form polymers is known as polymerization. ROMP (ring-opening metathesis polymerization) is a chain-growth polymerization in which ring-opening takes place due to strain. It is also known as olefin-metathesis.

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Answer 3

Question

Chapter 18, Problem 18.72AP

Interpretation Introduction

(a)

Interpretation:

The structure of the endo−dicyclopentadiene is to be drawn.

Concept introduction:

A chemical reaction that involves [4+2] cycloaddition is known as Diels-Alder reaction. The reactant molecules that give rise to the product are diene and dienophile. The rate of reaction is fast when the electronegative group is attached to dienophile. In this type of reaction, syn addition takes place.

Interpretation Introduction

(b)

Interpretation:

The structure of the polymer formed when endo−dicyclopentadiene is subjected to ROMP is to be drawn. The reason as to why the polymer formed is strong is to be stated.

Concept introduction:

The process by which respective monomers combine to form polymers is known as polymerization. ROMP (ring-opening metathesis polymerization) is a chain-growth polymerization in which ring-opening takes place due to strain. It is also known as olefin-metathesis.

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Answer 4

Question

Chapter 18, Problem 18.72AP

Interpretation Introduction

(a)

Interpretation:

The structure of the endo−dicyclopentadiene is to be drawn.

Concept introduction:

A chemical reaction that involves [4+2] cycloaddition is known as Diels-Alder reaction. The reactant molecules that give rise to the product are diene and dienophile. The rate of reaction is fast when the electronegative group is attached to dienophile. In this type of reaction, syn addition takes place.

Interpretation Introduction

(b)

Interpretation:

The structure of the polymer formed when endo−dicyclopentadiene is subjected to ROMP is to be drawn. The reason as to why the polymer formed is strong is to be stated.

Concept introduction:

The process by which respective monomers combine to form polymers is known as polymerization. ROMP (ring-opening metathesis polymerization) is a chain-growth polymerization in which ring-opening takes place due to strain. It is also known as olefin-metathesis.

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Answer 5

Chapter 18, Problem 18.72AP

Interpretation Introduction

(a)

Interpretation:

The structure of the endo−dicyclopentadiene is to be drawn.

Concept introduction:

A chemical reaction that involves [4+2] cycloaddition is known as Diels-Alder reaction. The reactant molecules that give rise to the product are diene and dienophile. The rate of reaction is fast when the electronegative group is attached to dienophile. In this type of reaction, syn addition takes place.

Interpretation Introduction

(b)

Interpretation:

The structure of the polymer formed when endo−dicyclopentadiene is subjected to ROMP is to be drawn. The reason as to why the polymer formed is strong is to be stated.

Concept introduction:

The process by which respective monomers combine to form polymers is known as polymerization. ROMP (ring-opening metathesis polymerization) is a chain-growth polymerization in which ring-opening takes place due to strain. It is also known as olefin-metathesis.

Answer 6

Chapter 18, Problem 18.72AP

Interpretation Introduction

(a)

Interpretation:

The structure of the endo−dicyclopentadiene is to be drawn.

Concept introduction:

A chemical reaction that involves [4+2] cycloaddition is known as Diels-Alder reaction. The reactant molecules that give rise to the product are diene and dienophile. The rate of reaction is fast when the electronegative group is attached to dienophile. In this type of reaction, syn addition takes place.

Answer 7

Chapter 18, Problem 18.72AP

Interpretation Introduction

(a)

Interpretation:

The structure of the endo−dicyclopentadiene is to be drawn.

Concept introduction:

A chemical reaction that involves [4+2] cycloaddition is known as Diels-Alder reaction. The reactant molecules that give rise to the product are diene and dienophile. The rate of reaction is fast when the electronegative group is attached to dienophile. In this type of reaction, syn addition takes place.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The structure of the polymer formed when endo−dicyclopentadiene is subjected to ROMP is to be drawn. The reason as to why the polymer formed is strong is to be stated.

Concept introduction:

The process by which respective monomers combine to form polymers is known as polymerization. ROMP (ring-opening metathesis polymerization) is a chain-growth polymerization in which ring-opening takes place due to strain. It is also known as olefin-metathesis.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The structure of the polymer formed when endo−dicyclopentadiene is subjected to ROMP is to be drawn. The reason as to why the polymer formed is strong is to be stated.

Concept introduction:

The process by which respective monomers combine to form polymers is known as polymerization. ROMP (ring-opening metathesis polymerization) is a chain-growth polymerization in which ring-opening takes place due to strain. It is also known as olefin-metathesis.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 18 - Prob. 18.1P Ch. 18 - Prob. 18.2P Ch. 18 - Prob. 18.3P Ch. 18 - Prob. 18.4P Ch. 18 - Prob. 18.5P Ch. 18 - Prob. 18.6P Ch. 18 - Prob. 18.7P Ch. 18 - Prob. 18.8P Ch. 18 - Prob. 18.9P Ch. 18 - Prob. 18.10P

Solution Summary: The author explains that the structure of endo-dicyclopentadiene is to be drawn.

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Chapter 18 Solutions