(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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Put the following compounds in order from weakest acid to strongest acid. Explain (pKa values are not enough and trends should be considered).

The preceding equation for the protonation of acetamide shows a hypothetical product that is not actually formed. When acetamide is protonated by a strong enough acid, it does not protonate on nitrogen, but at a different basic site. Draw the structure of the actual conjugate acid of acetamide, and explain (resonance) why protonation occurs where it does rather than on nitrogen. Calculate the pKa of this conjugate acid.

Acetic acid can also react as a very weak base (pKb = 20). Two different sites on acetic acid might become protonated to give the conjugate acid. Draw both of these possible conjugate acids, and explain (resonance) why the correct one is more stable. Calculate the pKa of this conjugate acid.

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 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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