Domanda del libro di testo
Which of the following compounds reacts with HBr more rapidly?
1144
views
Ch. 18 - Reactions of Benzene and Substituted Benzenes
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Non è quello che usi tu?Cambia libro di testoScegli un libro di testo diverso
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
Tutti i libri di testo
Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 65a
Bruice 8th EditionCh. 18 - Reactions of Benzene and Substituted BenzenesProblema 65aCapitolo 18, Problema 65a
Show how the following compounds can be synthesized from benzene:
a. N,N,N-trimethylanilinium iodide
Guida verificata passo dopo passo1
Step 1: Begin with benzene as the starting material. Perform a Friedel-Crafts alkylation reaction using methyl chloride (CH₃Cl) and aluminum chloride (AlCl₃) as a catalyst to introduce a methyl group onto the benzene ring, forming toluene (methylbenzene).
Step 2: Oxidize the methyl group on toluene to a carboxylic acid group using an oxidizing agent such as potassium permanganate (KMnO₄) under acidic or basic conditions. This converts toluene into benzoic acid.
Step 3: Reduce the carboxylic acid group on benzoic acid to an amine group (-NH₂) using a reaction such as the Schmidt reaction or by converting the acid to an amide followed by reduction with lithium aluminum hydride (LiAlH₄). This forms aniline (C₆H₅NH₂).
Step 4: Perform a methylation reaction on the aniline using excess methyl iodide (CH₃I) in the presence of a base such as potassium carbonate (K₂CO₃). This introduces three methyl groups onto the nitrogen atom, forming N,N,N-trimethylaniline.
Step 5: React N,N,N-trimethylaniline with methyl iodide (CH₃I) to quaternize the nitrogen atom, forming N,N,N-trimethylanilinium iodide as the final product.
Risposta video verificata per un problema simile:
Questa soluzione video è stata consigliata dai nostri tutor come utile per risolvere questo problema.
Durata del video:
8mConcetti chiave
Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.
Electrophilic Aromatic Substitution (EAS)
Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the synthesis of N,N,N-trimethylanilinium iodide from benzene, the first step involves the introduction of a nitrogen-containing electrophile, which forms a substituted aromatic compound. This reaction is crucial for modifying aromatic compounds to create more complex structures.
Video consigliato:
03:07
EAS Review
Quaternization of Amines
Quaternization of amines refers to the process of converting a tertiary amine into a quaternary ammonium salt by reacting it with an alkyl halide. In this case, the nitrogen atom in the aniline derivative formed from benzene is further reacted with methyl iodide to produce N,N,N-trimethylanilinium iodide. This step is essential for achieving the final product with the desired ionic character.
Video consigliato:
07:12Reductive Amination
Nucleophilicity and Electrophilicity
Nucleophilicity refers to the ability of a species to donate an electron pair, while electrophilicity is the ability to accept an electron pair. In the context of the reaction, the nitrogen atom in the amine acts as a nucleophile, attacking the electrophilic carbon of the alkyl halide (methyl iodide). Understanding these concepts is vital for predicting the outcome of reactions involving aromatic compounds and their derivatives.
Video consigliato:
03:Nucleophile or Electrophile
Pratica correlata
Domanda del libro di testo
Describe two ways to prepare anisole from benzene.
1844
views
Domanda del libro di testo
Use the four compounds shown below to answer the following questions:
a. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid?
1104
views
Domanda del libro di testo
Show how the following compounds can be synthesized from benzene:
g. p-dideuteriobenzene
897
views
Domanda del libro di testo
An aromatic hydrocarbon with a molecular formula of C13H20 has an 1H NMR spectrum with a signal at ~7 ppm that integrates to 5H. It also has two singlets; one of the singlets has 1.5 times the area of the second. What is the structure of the aromatic hydrocarbon?
1236
views
Domanda del libro di testo
Show how the following compounds can be synthesized from benzene:
h. p-nitro-N-methylaniline
960
views