Textbook Question
Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
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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 11f
Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(f) allyl iodide → but-3-enoic acid
Verified step by step guidance1
Step 1: Begin by identifying the functional groups in the starting material (allyl iodide) and the target molecule (but-3-enoic acid). Allyl iodide contains an alkyl halide group, while but-3-enoic acid contains a carboxylic acid group and a double bond.
Step 2: Plan the synthesis by considering the transformation of the alkyl halide into a carboxylic acid. A common method involves converting the alkyl halide into a Grignard reagent, which can then react with carbon dioxide to form a carboxylic acid.
Step 3: React allyl iodide with magnesium in dry ether to form allyl magnesium iodide, a Grignard reagent. The reaction can be represented as:
Step 4: Bubble carbon dioxide gas through the Grignard reagent solution to form the carboxylic acid intermediate. The reaction can be represented as:
Step 5: Perform an acidic workup (e.g., using dilute HCl) to protonate the carboxylate ion and isolate the final product, but-3-enoic acid. This step ensures the carboxylic acid is fully formed and purified.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Carboxylic Acid Synthesis
Carboxylic acids can be synthesized through various methods, including oxidation of alcohols, hydrolysis of nitriles, and carbon chain elongation. Understanding the functional groups and reactivity of starting materials is crucial for determining the appropriate synthetic route. In this case, the transformation of allyl iodide to but-3-enoic acid involves strategic manipulation of carbon skeletons and functional groups.
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Carboxylic Acids Nomenclature
Allyl Iodide Reactivity
Allyl iodide is a reactive alkyl halide that can undergo nucleophilic substitution and elimination reactions. Its structure allows for the formation of a double bond through elimination, which is essential for synthesizing alkenes. Recognizing how allyl iodide can be transformed into intermediates that lead to the desired carboxylic acid is key to solving the synthesis problem.
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Carbon Chain Elongation
Carbon chain elongation involves adding carbon atoms to a molecule, often through reactions like Grignard reactions or alkylation. In the context of synthesizing but-3-enoic acid, understanding how to extend the carbon chain from allyl iodide and subsequently introduce a carboxylic acid functional group is vital. This concept is fundamental in organic synthesis for constructing complex molecules from simpler precursors.
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Related Practice
Textbook Question
The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in an equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH2CH3.
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Textbook Question
Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(a) oct-4-yne → butanoic acid
(b) trans-cyclodecene → decanedioic acid
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Textbook Question
Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(e) p-xylene → terephthalic acid
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Textbook Question
A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.
(a) Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
(b) Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
(c) Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.
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Textbook Question
Show how you would synthesize the following carboxylic acids, using the indicated starting materials.
(d) butan-2-ol → 2-methylbutanoic acid