(a) Interpretation: The pKa value for a protonated amine ( R 3 NH + ) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. From least acidic to most acidic, the order that would be predicted using charge stability is to be determined. Concept introduction: The stability of a charged species depends on the groups attached to the positively charged atom. The electron withdrawing group increases the concentration of positive charge on the nearby atom. While, the electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge.

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Answer 1

Question

Chapter 6, Problem 6.88P

Interpretation Introduction

(a)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. From least acidic to most acidic, the order that would be predicted using charge stability is to be determined.

Concept introduction:

The stability of a charged species depends on the groups attached to the positively charged atom. The electron withdrawing group increases the concentration of positive charge on the nearby atom. While, the electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge.

Interpretation Introduction

(b)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. The reason for the discrepancy is to be explained.

Concept introduction:

The stability of a charged species decreases as the effective electronegativity of an atom bearing a positive charge increases. The electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge. Bulky group around the cation, reduces the solvation process. This decreases the stability of the ion and increases acidity.

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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+

Li+ is a hard acid. With this in mind, which if the following compounds should be most soluble in water? Group of answer choices LiBr LiI LiF LiCl

Answer 2

Question

Chapter 6, Problem 6.88P

Interpretation Introduction

(a)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. From least acidic to most acidic, the order that would be predicted using charge stability is to be determined.

Concept introduction:

The stability of a charged species depends on the groups attached to the positively charged atom. The electron withdrawing group increases the concentration of positive charge on the nearby atom. While, the electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge.

Interpretation Introduction

(b)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. The reason for the discrepancy is to be explained.

Concept introduction:

The stability of a charged species decreases as the effective electronegativity of an atom bearing a positive charge increases. The electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge. Bulky group around the cation, reduces the solvation process. This decreases the stability of the ion and increases acidity.

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Answer 3

Question

Chapter 6, Problem 6.88P

Interpretation Introduction

(a)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. From least acidic to most acidic, the order that would be predicted using charge stability is to be determined.

Concept introduction:

The stability of a charged species depends on the groups attached to the positively charged atom. The electron withdrawing group increases the concentration of positive charge on the nearby atom. While, the electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge.

Interpretation Introduction

(b)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. The reason for the discrepancy is to be explained.

Concept introduction:

The stability of a charged species decreases as the effective electronegativity of an atom bearing a positive charge increases. The electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge. Bulky group around the cation, reduces the solvation process. This decreases the stability of the ion and increases acidity.

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Answer 4

Question

Chapter 6, Problem 6.88P

Interpretation Introduction

(a)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. From least acidic to most acidic, the order that would be predicted using charge stability is to be determined.

Concept introduction:

The stability of a charged species depends on the groups attached to the positively charged atom. The electron withdrawing group increases the concentration of positive charge on the nearby atom. While, the electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge.

Interpretation Introduction

(b)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. The reason for the discrepancy is to be explained.

Concept introduction:

The stability of a charged species decreases as the effective electronegativity of an atom bearing a positive charge increases. The electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge. Bulky group around the cation, reduces the solvation process. This decreases the stability of the ion and increases acidity.

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Answer 5

Chapter 6, Problem 6.88P

Interpretation Introduction

(a)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. From least acidic to most acidic, the order that would be predicted using charge stability is to be determined.

Concept introduction:

The stability of a charged species depends on the groups attached to the positively charged atom. The electron withdrawing group increases the concentration of positive charge on the nearby atom. While, the electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge.

Interpretation Introduction

(b)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. The reason for the discrepancy is to be explained.

Concept introduction:

The stability of a charged species decreases as the effective electronegativity of an atom bearing a positive charge increases. The electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge. Bulky group around the cation, reduces the solvation process. This decreases the stability of the ion and increases acidity.

Answer 6

Chapter 6, Problem 6.88P

Interpretation Introduction

(a)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. From least acidic to most acidic, the order that would be predicted using charge stability is to be determined.

Concept introduction:

The stability of a charged species depends on the groups attached to the positively charged atom. The electron withdrawing group increases the concentration of positive charge on the nearby atom. While, the electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge.

Answer 7

Chapter 6, Problem 6.88P

Interpretation Introduction

(a)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. From least acidic to most acidic, the order that would be predicted using charge stability is to be determined.

Concept introduction:

The stability of a charged species depends on the groups attached to the positively charged atom. The electron withdrawing group increases the concentration of positive charge on the nearby atom. While, the electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. The reason for the discrepancy is to be explained.

Concept introduction:

The stability of a charged species decreases as the effective electronegativity of an atom bearing a positive charge increases. The electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge. Bulky group around the cation, reduces the solvation process. This decreases the stability of the ion and increases acidity.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. The reason for the discrepancy is to be explained.

Concept introduction:

The stability of a charged species decreases as the effective electronegativity of an atom bearing a positive charge increases. The electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge. Bulky group around the cation, reduces the solvation process. This decreases the stability of the ion and increases acidity.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 6 - Prob. 6.1P Ch. 6 - Prob. 6.2P Ch. 6 - Prob. 6.3P Ch. 6 - Prob. 6.4P Ch. 6 - Prob. 6.5P Ch. 6 - Prob. 6.6P Ch. 6 - Prob. 6.7P Ch. 6 - Prob. 6.8P Ch. 6 - Prob. 6.9P Ch. 6 - Prob. 6.10P

Solution Summary: The author explains that the pKa value for a protonated amine depends on the number of alkyl groups attached to N, which disagrees with what we would predict using charge stability.

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