The explanation corresponding to the given statement that addition of HBr across the double bond of 1 , 2 − dimethylcyclopentene is not stereospecific. Interpretation: The given question stated that addition of HBr across the double bond of 1 , 2 − dimethylcyclopentene gives mixture of cis and trans isomers. The addition is not stereospecific is to be predicted. Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene , whereas syn addition is the addition of atom from the same side.

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Answer 1

Question

Chapter 8.7C, Problem 8.16P

(a)

Interpretation Introduction

To determine: The explanation corresponding to the given statement that addition of HBr across the double bond of 1,2−dimethylcyclopentene is not stereospecific.

Interpretation: The given question stated that addition of HBr across the double bond of 1,2−dimethylcyclopentene gives mixture of cis and trans isomers. The addition is not stereospecific is to be predicted.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

(b)

Interpretation Introduction

To determine: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition.

Interpretation: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition is to be stated.

Concept introduction: Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-markovinokov’s rule.

Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

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In 4+2 cycloaddition, ENDO stereochemistry is preferred because: endo stereochemistry allows the diene to adopt s-cis conformation. endo stereochemistry results in less steric hindrance. the transition state leading to endo stereochemistry is higher energy. it allows for additional π to π overlap between the diene and the dienophile.

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.

(a) Draw the ring-flip isomer of the molecule. (b) Show which of the two is favored in the equilibrium between them, and explain why, showing all possible forms of strain in each of the isomers. (c) What is the stereochemical relationship between the two isomers? (d) Draw another stereoisomer of the molecule and show all the strains it contains.

Answer 2

Question

Chapter 8.7C, Problem 8.16P

(a)

Interpretation Introduction

To determine: The explanation corresponding to the given statement that addition of HBr across the double bond of 1,2−dimethylcyclopentene is not stereospecific.

Interpretation: The given question stated that addition of HBr across the double bond of 1,2−dimethylcyclopentene gives mixture of cis and trans isomers. The addition is not stereospecific is to be predicted.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

(b)

Interpretation Introduction

To determine: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition.

Interpretation: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition is to be stated.

Concept introduction: Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-markovinokov’s rule.

Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

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Answer 3

Question

Chapter 8.7C, Problem 8.16P

(a)

Interpretation Introduction

To determine: The explanation corresponding to the given statement that addition of HBr across the double bond of 1,2−dimethylcyclopentene is not stereospecific.

Interpretation: The given question stated that addition of HBr across the double bond of 1,2−dimethylcyclopentene gives mixture of cis and trans isomers. The addition is not stereospecific is to be predicted.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

(b)

Interpretation Introduction

To determine: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition.

Interpretation: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition is to be stated.

Concept introduction: Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-markovinokov’s rule.

Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

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Answer 4

Question

Chapter 8.7C, Problem 8.16P

(a)

Interpretation Introduction

To determine: The explanation corresponding to the given statement that addition of HBr across the double bond of 1,2−dimethylcyclopentene is not stereospecific.

Interpretation: The given question stated that addition of HBr across the double bond of 1,2−dimethylcyclopentene gives mixture of cis and trans isomers. The addition is not stereospecific is to be predicted.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

(b)

Interpretation Introduction

To determine: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition.

Interpretation: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition is to be stated.

Concept introduction: Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-markovinokov’s rule.

Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

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Answer 5

Chapter 8.7C, Problem 8.16P

(a)

Interpretation Introduction

To determine: The explanation corresponding to the given statement that addition of HBr across the double bond of 1,2−dimethylcyclopentene is not stereospecific.

Interpretation: The given question stated that addition of HBr across the double bond of 1,2−dimethylcyclopentene gives mixture of cis and trans isomers. The addition is not stereospecific is to be predicted.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

(b)

Interpretation Introduction

To determine: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition.

Interpretation: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition is to be stated.

Concept introduction: Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-markovinokov’s rule.

Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

Answer 6

Chapter 8.7C, Problem 8.16P

(a)

Interpretation Introduction

To determine: The explanation corresponding to the given statement that addition of HBr across the double bond of 1,2−dimethylcyclopentene is not stereospecific.

Interpretation: The given question stated that addition of HBr across the double bond of 1,2−dimethylcyclopentene gives mixture of cis and trans isomers. The addition is not stereospecific is to be predicted.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

Answer 7

Chapter 8.7C, Problem 8.16P

(a)

Interpretation Introduction

To determine: The explanation corresponding to the given statement that addition of HBr across the double bond of 1,2−dimethylcyclopentene is not stereospecific.

Interpretation: The given question stated that addition of HBr across the double bond of 1,2−dimethylcyclopentene gives mixture of cis and trans isomers. The addition is not stereospecific is to be predicted.

Concept introduction: Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

Answer 8

(b)

Interpretation Introduction

To determine: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition.

Interpretation: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition is to be stated.

Concept introduction: Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-markovinokov’s rule.

Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

Answer 9

(b)

Interpretation Introduction

To determine: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition.

Interpretation: The major product when 1,2−dimethylcyclopentene undergoes hydroboration-oxidation and explanation corresponding to stereospecific addition is to be stated.

Concept introduction: Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-markovinokov’s rule.

Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

Answer 10

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Answer 13

Ch. 8.3A - Predict the major products of the following...Ch. 8.3A - a. When 1 mole of buta-1,3-diene reacts with 1...Ch. 8.3B - Predict the major products of the following...Ch. 8.3B - Show how you would accomplish the following...Ch. 8.4B - Propose a mechanism to show how...Ch. 8.4B - Predict the products of the following hydration...Ch. 8.6 - a. Propose a mochansm fortho following reaction....Ch. 8.6 - Prob. 8.8P Ch. 8.6 - Prob. 8.9P Ch. 8.7A - Prob. 8.10P

Solution Summary: The author explains that the addition of HBr across the double bond is not stereospecific. The attack of bromide ion over planar carbocation can be either from front side or from

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