Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 2, Problem 2.54SP

(a)

Interpretation Introduction

To determine: The four different conjugate bases that would be formed by the deprotonation of the four different OH groups in ascorbic acid.

Interpretation: The four different conjugate bases that would be formed by the deprotonation of the four different OH groups in ascorbic acid are to be shown.

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. When an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid.

(b)

Interpretation Introduction

To determine: The comparison between the stabilities of the resulting conjugate bases and the most acidic OH group of ascorbic acid.

Interpretation: The stabilities of the resulting conjugate bases are to be compared and the most acidic OH group of ascorbic acid is to be predicted.

Concept introduction: The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.

(c)

Interpretation Introduction

To determine: The comparison between the most stable conjugate bases of ascorbic acid and acetic acid and an explanation corresponding to the fact that the two compounds have similar acidities even though ascorbic acid lacks carboxylic group.

Interpretation: The most stable conjugate bases of ascorbic acid and acetic acid are to be compared and an explanation corresponding to the fact that the two compounds have similar acidities even though ascorbic acid lacks carboxylic group is to be explained.

Concept introduction: The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.

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Chapter 2 Solutions

Organic Chemistry (9th Edition)

Ch. 2.7 - Ethanol, methylamine. and acetic acid are all...Ch. 2.8 - Prob. 2.12PCh. 2.10 - Write equations for the following acid-base...Ch. 2.10 - Rank the following acids in decreasing order of...Ch. 2.11 - Prob. 2.15PCh. 2.11 - Prob. 2.16PCh. 2.11 - Consider each pair of bases and explain which one...Ch. 2.12 - Which is a stronger base ethoxide ion or acetate...Ch. 2.12 - Prob. 2.19PCh. 2.12 - Prob. 2.20PCh. 2.12 - Prob. 2.21PCh. 2.12 - Choose the more basic member of each pair of...Ch. 2.14 - Prob. 2.23PCh. 2.15D - Classify the following hydrocarbons and draw a...Ch. 2.16D - Prob. 2.25PCh. 2.17C - Draw a Lewis structure and classify each of the...Ch. 2.17C - Circle the functional groups in the following...Ch. 2 - The CN triple bond in acetonitrile has a dipole...Ch. 2 - Prob. 2.29SPCh. 2 - Sulfur dioxide has a dipole moment of 1.60 D....Ch. 2 - Which of the following pure compounds can form...Ch. 2 - Predict which member of each pair is more soluble...Ch. 2 - Prob. 2.33SPCh. 2 - Prob. 2.34SPCh. 2 - Predict which compound in each pair has the higher...Ch. 2 - All of the following compounds can react as acids...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - The Ka of phenylacetic acid is 5 2 105, and the...Ch. 2 - The following compound can become protonated on...Ch. 2 - The following compounds are listed in increasing...Ch. 2 - Prob. 2.42SPCh. 2 - Prob. 2.43SPCh. 2 - Compare the relative acidity of 1-molar aqueous...Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - The following compounds can all react as bases. a....Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - Prob. 2.48SPCh. 2 - Methyllithium (CH3Li) is often used as a base in...Ch. 2 - Label the reactants in these acid-base reactions...Ch. 2 - In each reaction, label the reactants as Lewis...Ch. 2 - Prob. 2.52SPCh. 2 - Each of these compounds can react as a nucleophile...Ch. 2 - Prob. 2.54SPCh. 2 - Give a definition and an example for each class of...Ch. 2 - Circle the functional groups in the following...Ch. 2 - Prob. 2.57SP
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