Textbook Question
Show how Friedel–Crafts acylation might be used to synthesize the following compounds.
c. n-butylbenzene
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Ch. 21 - Carboxylic Acid Derivatives
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 21, Problem 34a
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(a) 
Verified step by step guidance1
Step 1: Analyze the transformation. The starting material is salicylic acid (a benzene ring with an -OH group and a -COOH group in ortho positions). The product is acetylsalicylic acid (aspirin), where the -OH group has been converted into an ester (-OCOCH3).
Step 2: Recognize the type of reaction. This is an esterification reaction, where the hydroxyl group (-OH) reacts with an acylating agent to form an ester.
Step 3: Identify the appropriate reagent. Acetic anhydride (CH3CO)2O is commonly used for acetylation reactions because it reacts efficiently with alcohols to form esters.
Step 4: Explain the mechanism. In the presence of a catalyst like sulfuric acid or phosphoric acid, acetic anhydride reacts with the hydroxyl group of salicylic acid. The acyl group (CH3CO-) is transferred to the -OH group, forming the ester bond.
Step 5: Note reaction conditions. The reaction typically requires mild heating to ensure the acetylation proceeds efficiently, and the catalyst helps to speed up the reaction by protonating the acetic anhydride, making it more reactive.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reagent Selection in Organic Synthesis
Choosing the right reagent is crucial in organic synthesis as it determines the efficiency and outcome of the reaction. Factors such as the desired product, reaction conditions, and the functional groups present in the reactants must be considered. Understanding the reactivity and selectivity of different reagents helps in predicting the formation of the desired product.
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Synthesis of Amino Acids: Strecker Synthesis Example 1
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying the functional groups in the reactants and products is essential for selecting appropriate reagents, as different functional groups react differently under various conditions. This knowledge aids in predicting the pathways and mechanisms of the synthesis.
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Reaction Mechanisms
A reaction mechanism describes the step-by-step process by which reactants are converted into products. Understanding mechanisms is vital for predicting the outcomes of reactions and for rationalizing the choice of reagents. Knowledge of mechanisms also helps in identifying potential side reactions and optimizing conditions for the desired synthesis.
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Related Practice
Textbook Question
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(c)
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Textbook Question
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(b)
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Textbook Question
Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.
(c) phthalic acid monoamide
(d) succinic acid monomethyl ester
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Textbook Question
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(d)
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Textbook Question
Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.
(a) n-octyl formate
(b) n-octyl acetate
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