(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.

Question

Want to see the full answer?

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Using pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.

но HO но он The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic than acetic acid (CH3CO0H, pKa 4.74). (a) Show the fou r different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid. (b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic. (c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.

The C-H bond in acetone, (CH3)C=O, has a pką of 19.2. Draw two resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, CH;CH,CH3 (pKa = 50). %3D

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Concept explainers

Videos

Want to see the full answer?

Chapter 6 Solutions