Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 2.12, Problem 2.19P
Interpretation Introduction
Interpretation: The structure of the conjugate acid of acetamide is to be drawn. An explanation corresponding to the fact that in acetamide protonation does not occur at nitrogen is to be explained. The
Concept introduction: According to Bronsted-Lowry theory, 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. The conjugate base has negative charge or lone pair of electrons present over it.
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. The delocalization of electrons due to presence of lone pair and double bond is called resonating structure.
To determine: The structure of the conjugate acid of acetamide,
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Why is the N-H bond of an imide especially acidic?
A) The conjugate acid is stabilized by resonance.
B) The conjugate base is stabilized by resonance.
The conjugate base is stabilized by
(c)
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The conjugate base is stabilized by electron-
(D
donating inductive effect.
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.
Rank the following bases in order of increasing basicity: LDA, cyclohexane magnesium chloride, NaOme, benzylamine, water.
Chapter 2 Solutions
Organic Chemistry (9th Edition)
Ch. 2.1A - Prob. 2.1PCh. 2.1B - The NF bond is more polar than the NH bond: but...Ch. 2.1B - For each of the following compounds 1. Draw the...Ch. 2.1B - Two isomers of 1,2-dichloroethene are known One...Ch. 2.2C - Prob. 2.5PCh. 2.2C - Prob. 2.6PCh. 2.3 - Prob. 2.7PCh. 2.4 - Calculate the pH of the following solutions a....Ch. 2.6A - Ammonia appears in Table 2-2 as both an acid and a...Ch. 2.7 - Write equations for the following acid-base...
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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