(a) Interpretation: The major product of the given reaction is to be predicted. Concept introduction: A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br · radical. Br · radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

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Answer 1

Question

Chapter 25, Problem 25.20P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

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What are the IUPAC Names of all the compounds in the picture?

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 25, Problem 25.20P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

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Answer 3

Question

Chapter 25, Problem 25.20P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

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Answer 4

Question

Chapter 25, Problem 25.20P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

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Answer 5

Chapter 25, Problem 25.20P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

Answer 6

Chapter 25, Problem 25.20P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

Answer 7

Chapter 25, Problem 25.20P

Interpretation Introduction

(a)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The major product of the given reaction is to be predicted.

Concept introduction:

A hydrogen halide adds across the double bond of an alkene in the presence of peroxide; the H atom adds to the more substituted C, and the halide atom adds to the less substituted one. This is an anti-Markovnikov addition. HBr and peroxide are sources of Br· radical. Br· radical adds to the alkene via radical addition, and the resulting alkyl radical abstracts a H atom from HBr, yielding the overall product. The more substituted alkyl radical forms C-H bond. Thus, the addition is anti-Markovnikov addition.

Answer 10

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Answer 13

Ch. 25 - Prob. 25.1P Ch. 25 - Prob. 25.2P Ch. 25 - Prob. 25.3P Ch. 25 - Prob. 25.4P Ch. 25 - Prob. 25.5P Ch. 25 - Prob. 25.6P Ch. 25 - Prob. 25.7P Ch. 25 - Prob. 25.8P Ch. 25 - Prob. 25.9P Ch. 25 - Prob. 25.10P

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Chapter 25 Solutions