Textbook Question
Predict the products (if any) of the following acid–base reactions.
(d) α-bromopropionic acid + sodium propionate
(e) benzoic acid + sodium phenoxide
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Ch. 20 - Carboxylic Acids
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 20, Problem 30a,b,c
Predict the products (if any) of the following acid–base reactions.
(a) acetic acid + ammonia
(b) phthalic acid + excess NaOH
(c) p-toluic acid + potassium trifluoroacetate
Verified step by step guidance1
Step 1: Understand the nature of acid-base reactions. Acid-base reactions involve the transfer of a proton (H⁺) from the acid to the base. Acids are proton donors, and bases are proton acceptors. Identify the acid and base in each reaction.
Step 2: For (a) acetic acid + ammonia: Acetic acid (CH₃COOH) is a weak acid, and ammonia (NH₃) is a weak base. The reaction involves the transfer of a proton from acetic acid to ammonia, forming ammonium ion (NH₄⁺) and acetate ion (CH₃COO⁻). Write the balanced chemical equation:
Step 3: For (b) phthalic acid + excess NaOH: Phthalic acid is a diprotic acid (C₆H₄(COOH)₂). In the presence of excess NaOH, both acidic protons are neutralized, forming the disodium salt of phthalic acid (C₆H₄(COONa)₂) and water. Write the balanced chemical equation:
Step 4: For (c) p-toluic acid + potassium trifluoroacetate: p-Toluic acid (C₆H₄(CH₃)(COOH)) is a weak acid, and potassium trifluoroacetate (CF₃COOK) is a weak base. The reaction involves the transfer of a proton from p-toluic acid to trifluoroacetate ion (CF₃COO⁻), forming trifluoroacetic acid (CF₃COOH) and the potassium salt of p-toluic acid (C₆H₄(CH₃)(COOK)). Write the balanced chemical equation:
Step 5: Verify the products for each reaction. Ensure that the acid donates a proton to the base, and the resulting conjugate acid and conjugate base are correctly identified. Confirm that the stoichiometry of each reaction is balanced.
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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+) from an acid to a base. In these reactions, acids are proton donors, while bases are proton acceptors. Understanding the strength of the acids and bases involved is crucial, as it influences the direction of the reaction and the stability of the products formed.
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02:49
The Lewis definition of acids and bases.
Dissociation of Acids and Bases
Acids and bases dissociate in solution to form ions. For example, acetic acid (CH3COOH) dissociates into acetate ions (CH3COO-) and protons (H+). The extent of dissociation depends on the acid's strength; strong acids dissociate completely, while weak acids only partially dissociate. This concept is essential for predicting the products of the reactions.
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02:49The Lewis definition of acids and bases.
Neutralization Reactions
Neutralization reactions occur when an acid reacts with a base to form water and a salt. In the context of the given question, identifying the products involves recognizing how the acid and base interact, leading to the formation of new compounds. For example, when phthalic acid reacts with NaOH, the result is the formation of a salt and water, illustrating the neutralization process.
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Related Practice
Textbook Question
Draw the structures of the following compounds.
(f) salicylic acid
(g) zinc undecanoate (athlete's-foot powder)
(h) sodium benzoate (a food preservative)
(i) sodium fluoroacetate (Compound 1080, a controversial coyote poison)
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Textbook Question
Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoic acid, phenol, benzyl alcohol, aniline
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Textbook Question
Arrange each group of compounds in order of increasing acidity.
(a) phenol, ethanol, acetic acid
(b) p-toluenesulfonic acid, acetic acid, chloroacetic acid
(c) benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acid
(d) butyric acid, α-bromobutyric acid, β-bromobutyric acid
(e)
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Textbook Question
Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.
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Textbook Question
Arrange each group of compounds in order of increasing basicity.
c. sodium benzoate, sodium ethoxide, and sodium phenoxide
d. pyridine, sodium ethoxide, and sodium acetate
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