Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
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Chapter 22, Problem 22.60SP

(1)

Interpretation Introduction

Interpretation:

The most acidic hydrogens in the given compounds are to be indicated.

Concept introduction:

The substances that produce hydrogen ions (H+) on dissociation are known as acids. The substances that produce hydroxide ions (OH) on dissociation are known as bases. The concept of acids and bases was expanded by Johannes Bronsted and Thomas Lowry in the early twentieth century.

According to the definition of Bronsted and Lowry, acids are the substances that donate protons whereas bases are the substances that accept protons.

(1)

Expert Solution
Check Mark

Answer to Problem 22.60SP

The most acidic hydrogens in the given compounds are shown in Figure 1.

Explanation of Solution

In a molecule, different types of protons are present. However, when acting as acids, only the most acidic proton participates in the acid-base reaction. The protons of functional groups are most acidic in nature as they are easily available for donation.

Acidic hydrogen is defined as that hydrogen which is attached to more electronegative atoms like oxygen and fluorine. The compound (f) does not contain any acidic hydrogen atom in the given compounds.

The most acidic hydrogens in the given compounds are shown below.

Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition, Chapter 22, Problem 22.60SP , additional homework tip  1

Figure 1

(2)

Interpretation Introduction

Interpretation:

The structures of important resonance contributors of the anions of the given compounds are to be drawn.

Concept introduction:

The delocalization of electrons due to presence of lone pair and double bond is called resonating structure. The structure is more stable if the resonating structures are more.

(2)

Expert Solution
Check Mark

Answer to Problem 22.60SP

The structures of important resonance contributors of the anions of the given compounds are shown below.

Explanation of Solution

The formation of carbanion occurs when acidic hydrogen is removed from a compound. The important resonance contributors of the anions that results from the removal of most acidic hydrogen are shown below.

(a)

Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition, Chapter 22, Problem 22.60SP , additional homework tip  2

Figure 2

(b)

Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition, Chapter 22, Problem 22.60SP , additional homework tip  3

Figure 3

(c)

Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition, Chapter 22, Problem 22.60SP , additional homework tip  4

Figure 4

(d)

Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition, Chapter 22, Problem 22.60SP , additional homework tip  5

Figure 5

(e)

Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition, Chapter 22, Problem 22.60SP , additional homework tip  6

Figure 6

(f)

The given compound is shown below.

Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition, Chapter 22, Problem 22.60SP , additional homework tip  7

Figure 7

The given compound does not contain any acidic hydrogen atom. Therefore, it does not show resonance structures.

(g)

Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition, Chapter 22, Problem 22.60SP , additional homework tip  8

Figure 8

(h)

Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition, Chapter 22, Problem 22.60SP , additional homework tip  9

Figure 9

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Chapter 22 Solutions

Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition

Ch. 22.5C - Acid-catalyzed halogenation is synthetically...Ch. 22.6 - Show the products of the reactions of these...Ch. 22.7A - Prob. 22.18PCh. 22.7A - Prob. 22.19PCh. 22.7A - Prob. 22.20PCh. 22.7B - Prob. 22.21PCh. 22.8 - Prob. 22.22PCh. 22.8 - Prob. 22.24PCh. 22.9 - Prob. 22.25PCh. 22.9 - Prob. 22.26PCh. 22.9 - Prob. 22.27PCh. 22.9 - Prob. 22.28PCh. 22.9 - Prob. 22.29PCh. 22.10 - When cyclodecane-1,6-dione is treated with sodium...Ch. 22.11 - Prob. 22.32PCh. 22.11 - Prob. 22.33PCh. 22.12 - Prob. 22.34PCh. 22.12 - Prob. 22.35PCh. 22.12 - Prob. 22.36PCh. 22.12 - Prob. 22.37PCh. 22.12 - Show what esters would undergo Claisen...Ch. 22.13 - Prob. 22.39PCh. 22.13 - Prob. 22.40PCh. 22.14 - Prob. 22.41PCh. 22.14 - Prob. 22.42PCh. 22.14 - Show how crossed Claisen condensations could be...Ch. 22.14 - Prob. 22.44PCh. 22.14 - Prob. 22.45PCh. 22.15 - Prob. 22.46PCh. 22.16 - Prob. 22.47PCh. 22.16 - Prob. 22.48PCh. 22.17 - Prob. 22.49PCh. 22.17 - Prob. 22.50PCh. 22.17 - Prob. 22.51PCh. 22.18 - Prob. 22.52PCh. 22.18 - Prob. 22.53PCh. 22.18 - Prob. 22.54PCh. 22.18 - Prob. 22.55PCh. 22.18 - Prob. 22.56PCh. 22.19 - Prob. 22.57PCh. 22.19 - Prob. 22.58PCh. 22.19 - Prob. 22.59PCh. 22 - Prob. 22.60SPCh. 22 - 1. Rank the following compounds in order of...Ch. 22 - Prob. 22.62SPCh. 22 - Prob. 22.63SPCh. 22 - Prob. 22.64SPCh. 22 - Pentane-2,4-dione (acetylacetone) exists as a...Ch. 22 - a. Rank these compounds in order of increasing...Ch. 22 - Prob. 22.67SPCh. 22 - Prob. 22.68SPCh. 22 - 22-69 Predict the products of the following...Ch. 22 - Predict the products of these reaction sequences.Ch. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.72SPCh. 22 - Prob. 22.73SPCh. 22 - Prob. 22.74SPCh. 22 - The Knoevenagel condensation is a special case of...Ch. 22 - Prob. 22.76SPCh. 22 - Propose mechanisms for the following reactions.Ch. 22 - Prob. 22.78SPCh. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.80SPCh. 22 - Propose a mechanism for the following reaction....Ch. 22 - Prob. 22.83SPCh. 22 - Prob. 22.84SPCh. 22 - Prob. 22.85SP
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