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Draw a structure for each of the following:
d. m-chlorobenzonitrile
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Ch. 18 - Reactions of Benzene and Substituted Benzenes
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 4
Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 4Capitolo 18, Problema 4
Show the mechanism for the generation of the acylium ion if an acid anhydride is used instead of an acyl chloride for the source of the acylium ion.
Guida verificata passo dopo passo1
Step 1: Recognize that the acid anhydride is the source of the acylium ion. Acid anhydrides are compounds with two acyl groups bonded to an oxygen atom. In this case, the acid anhydride reacts with a Lewis acid catalyst, AlCl₃, to generate the acylium ion.
Step 2: The Lewis acid, AlCl₃, interacts with one of the carbonyl oxygen atoms in the acid anhydride. This interaction increases the electrophilicity of the carbonyl carbon, making it more susceptible to nucleophilic attack.
Step 3: A cleavage occurs in the acid anhydride. The bond between the carbonyl carbon and the oxygen atom breaks, resulting in the formation of the acylium ion (R-C≡O⁺) and a carboxylate ion (R-COO⁻). The acylium ion is stabilized by resonance, where the positive charge is delocalized between the carbon and oxygen atoms.
Step 4: The carboxylate ion formed in the previous step can coordinate with the AlCl₃ catalyst, forming a complex. This complex stabilizes the carboxylate ion and prevents it from interfering with the reaction.
Step 5: The acylium ion is now available to participate in electrophilic aromatic substitution reactions, such as Friedel-Crafts acylation, where it reacts with the benzene ring to form an aromatic ketone.
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Acylium Ion Formation
The acylium ion is a resonance-stabilized cation formed from acyl compounds, such as acyl chlorides or acid anhydrides. In the presence of a Lewis acid like AlCl3, the carbonyl carbon of the acyl compound becomes electrophilic, allowing for the generation of the acylium ion. This ion is crucial in electrophilic aromatic substitution reactions, particularly in Friedel-Crafts acylation.
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Percorso guidato
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Metal Ion Catalysis Concept 1
Friedel-Crafts Acylation
Friedel-Crafts acylation is a reaction that introduces an acyl group into an aromatic ring using an acylium ion. The process involves the electrophilic attack of the acylium ion on the aromatic system, followed by deprotonation to restore aromaticity. This reaction is significant for synthesizing ketones from aromatic compounds and is facilitated by Lewis acids that activate the acylium ion.
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05:20Friedel-Crafts Acylation
Acid Anhydrides vs. Acyl Chlorides
Acid anhydrides and acyl chlorides are both sources of acylium ions, but they differ in reactivity and byproducts. Acid anhydrides are generally less reactive than acyl chlorides, leading to milder reaction conditions. When using acid anhydrides, the reaction produces a carboxylic acid as a byproduct, while acyl chlorides yield hydrochloric acid. Understanding these differences is essential for predicting reaction outcomes in acylation processes.
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01:57Recognizing acyl chlorides and anhydrides.