Textbook Question
Predict the products of the following acid–base reactions.
(f)
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Ch. 2 - Acids and Bases; Functional Groups
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 2, Problem 42h
Predict the products of the following acid–base reactions.
(h) 
Verified step by step guidance1
Identify the acid and base in the reaction. In this case, +NH3CH2COOH is the acid, and -OH is the base.
Recognize that the acid, +NH3CH2COOH, has two acidic protons: one on the ammonium group (+NH3) and one on the carboxylic acid group (COOH).
Understand that the hydroxide ion (-OH) will deprotonate the most acidic proton first. Typically, the carboxylic acid proton is more acidic than the ammonium proton.
Write the deprotonation reaction of the carboxylic acid group: +NH3CH2COOH + -OH → +NH3CH2COO- + H2O.
Consider the possibility of further deprotonation. The ammonium group can also be deprotonated by another hydroxide ion: +NH3CH2COO- + -OH → NH2CH2COO- + H2O.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acid-Base Reactions
Acid-base reactions involve the transfer of protons (H+) between reactants. In this context, the amino acid +NH3CH2COOH acts as an acid, donating protons to the base, which is the hydroxide ion (OH-). Understanding the nature of acids and bases, including their ability to donate or accept protons, is crucial for predicting the products of such reactions.
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02:49
The Lewis definition of acids and bases.
Zwitterions
A zwitterion is a molecule with both positive and negative charges, but which is overall electrically neutral. Amino acids like +NH3CH2COOH can exist as zwitterions, where the amino group is protonated (+NH3) and the carboxyl group is deprotonated (COO-). Recognizing this form is essential for understanding how amino acids behave in different pH environments, especially in acid-base reactions.
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04:41Why Amino Acids Exist as Zwitterions
Deprotonation
Deprotonation is the removal of a proton (H+) from a molecule, resulting in the formation of a conjugate base. In the given reaction, the hydroxide ions (OH-) will deprotonate the amino acid, leading to the formation of water and the conjugate base of the amino acid. This process is key to predicting the products of the reaction, as it determines the new chemical species formed.
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Related Practice
Textbook Question
The following compounds can all react as acids.
a. For each compound, show its conjugate base. Show any resonance forms if applicable. b. Rank the conjugate bases in the order you would predict, from most stable to least stable.
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Textbook Question
Compare the relative acidity of 1-molar aqueous solutions of the following acids.
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Textbook Question
Consider the following proposed Brønsted–Lowry acid–base reactions. In each case, draw the products of a transfer of the most acidic proton on the acid to the most basic site on the base. Use Appendix 4 to find or estimate the pKa values for the acids and the pKb values for the bases. Then determine which side of the reaction is favored, either reactants or products.
(a)
(b)
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Textbook Question
Predict the products of the following acid–base reactions.
(g) HCOOH + CH3O– ⇌
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Textbook Question
Predict the products of the following acid–base reactions.
(g) HCOOH + CH3O– ⇌
(h) +NH3CH2COOH + 2 –OH ⇌
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