Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
Question
Book Icon
Chapter 3, Problem 36PP

(a)

Interpretation Introduction

Interpretation:

Conjugate bases of given acids are needed to be drawn.

Concept introduction:

According to Bronsted-Lowry concept, acid is a proton donor. The deprotonated acids are called conjugate base. The stability of this conjugate base determines the location of deprotonation in an acid.

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  1

In a conjugate base where the negative charge is carried by a more electronegative atom will show more stability. The greater electronegativity makes lone pair closer to the nucleus hence more stabilized.

The conjugate base having resonance will have greater stability as compared to conjugate base having single anion. Because of the resonance conjugate base will get resonance stabilization.

(a)

Expert Solution
Check Mark

Answer to Problem 36PP

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  2

Explanation of Solution

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  3

The most acidic proton of the given acid (a) is O-H proton, because deprotonation at oxygen gives a conjugate base having negative charge on oxygen atom, it is very much stable as compared to negative charge on carbon atom which is resulted by the deprotonation of any CH

(b)

Interpretation Introduction

Interpretation:

Conjugate bases of given acids are needed to be drawn.

Concept introduction:

According to Bronsted-Lowry concept, acid is a proton donor. The deprotonated acids are called conjugate base. The stability of this conjugate base determines the location of deprotonation in an acid.

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  4

In a conjugate base where the negative charge is carried by a more electronegative atom will show more stability. The greater electronegativity makes lone pair closer to the nucleus hence more stabilized.

The conjugate base having resonance will have greater stability as compared to conjugate base having single anion. Because of the resonance conjugate base will get resonance stabilization.

(b)

Expert Solution
Check Mark

Answer to Problem 36PP

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  5

Explanation of Solution

The most acidic hydrogen atom presented in the given acid is CH located adjacent to C=O . The deprotonation of this CH will results in the formation of a conjugate base will have resonance stabilization. This is shown below,

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  6.

No other CH deprotonation will give a conjugate base stable than above shown.

(c)

Interpretation Introduction

Interpretation:

Conjugate bases of given acids are needed to be drawn.

Concept introduction:

According to Bronsted-Lowry concept, acid is a proton donor. The deprotonated acids are called conjugate base. The stability of this conjugate base determines the location of deprotonation in an acid.

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  7

In a conjugate base where the negative charge is carried by a more electronegative atom will show more stability. The greater electronegativity makes lone pair closer to the nucleus hence more stabilized.

The conjugate base having resonance will have greater stability as compared to conjugate base having single anion. Because of the resonance conjugate base will get resonance stabilization.

(c)

Expert Solution
Check Mark

Answer to Problem 36PP

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  8

Explanation of Solution

Deprotonation of NH3 gives NH2 ,

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  9

(d)

Interpretation Introduction

Interpretation:

Conjugate bases of given acids are needed to be drawn.

Concept introduction:

According to Bronsted-Lowry concept, acid is a proton donor. The deprotonated acids are called conjugate base. The stability of this conjugate base determines the location of deprotonation in an acid.

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  10

In a conjugate base where the negative charge is carried by a more electronegative atom will show more stability. The greater electronegativity makes lone pair closer to the nucleus hence more stabilized.

The conjugate base having resonance will have greater stability as compared to conjugate base having single anion. Because of the resonance conjugate base will get resonance stabilization.

(d)

Expert Solution
Check Mark

Answer to Problem 36PP

     Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  11

Explanation of Solution

Deprotonation of H3O+ gives H2O ,

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  12

(e)

Interpretation Introduction

Interpretation:

Conjugate bases of given acids are needed to be drawn.

Concept introduction:

According to Bronsted-Lowry concept, acid is a proton donor. The deprotonated acids are called conjugate base. The stability of this conjugate base determines the location of deprotonation in an acid.

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  13

In a conjugate base where the negative charge is carried by a more electronegative atom will show more stability. The greater electronegativity makes lone pair closer to the nucleus hence more stabilized.

The conjugate base having resonance will have greater stability as compared to conjugate base having single anion. Because of the resonance conjugate base will get resonance stabilization.

(e)

Expert Solution
Check Mark

Answer to Problem 36PP

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  14

Explanation of Solution

The most acidic proton of the given acid (e) is O-H proton, because the deprotonation at oxygen gives a conjugate base having negative charge on oxygen atom. It is more stable than the negative charge on carbon atom which is resulted by the deprotonation of any CH . There is resonance stabilization after deprotonation of O-H in the conjugate base.

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  15

(f)

Interpretation Introduction

Interpretation:

Conjugate bases of given acids are needed to be drawn.

Concept introduction:

According to Bronsted-Lowry concept, acid is a proton donor. The deprotonated acids are called conjugate base. The stability of this conjugate base determines the location of deprotonation in an acid.

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  16

In a conjugate base where the negative charge is carried by a more electronegative atom will show more stability. The greater electronegativity makes lone pair closer to the nucleus hence more stabilized.

The conjugate base having resonance will have greater stability as compared to conjugate base having single anion. Because of the resonance conjugate base will get resonance stabilization.

(f)

Expert Solution
Check Mark

Answer to Problem 36PP

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  17

Explanation of Solution

The most acidic proton of the given acid (e) is NH2 proton, because deprotonation at nitrogen atom gives a conjugate base having negative charge on nitrogen atom, it is very much stable as compared to negative charge on carbon atom which is resulted by the deprotonation any CH in the above compound.

(g)

Interpretation Introduction

Interpretation:

Conjugate bases of given acids are needed to be drawn.

Concept introduction:

According to Bronsted-Lowry concept, acid is a proton donor. The deprotonated acids are called conjugate base. The stability of this conjugate base determines the location of deprotonation in an acid.

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  18

In a conjugate base where the negative charge is carried by a more electronegative atom will show more stability. The greater electronegativity makes lone pair closer to the nucleus hence more stabilized.

The conjugate base having resonance will have greater stability as compared to conjugate base having single anion. Because of the resonance conjugate base will get resonance stabilization.

(g)

Expert Solution
Check Mark

Answer to Problem 36PP

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  19

Explanation of Solution

Deprotonation of NH4+ gives NH3 ,

Organic Chemistry, Chapter 3, Problem 36PP , additional homework tip  20

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Knowledge Booster
Background pattern image
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY