Domanda del libro di testo
Propose mechanisms for the following reactions.
(a)
1122
views
Ch. 19 - Amines
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Non è quello che usi tu?Cambia libro di testoScegli un libro di testo diverso
TOC.tableOfContents
- 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
Capitolo 19, Problema 45c
Synthesize from benzene. (Hint: All of these require diazonium ions.)
(c) 2-methyl-5-hydroxybenzoic acid
Guida verificata passo dopo passo1
Start with benzene as the base compound. Perform a nitration reaction by treating benzene with a mixture of concentrated HNO₃ and H₂SO₄. This introduces a nitro group (-NO₂) to the benzene ring, forming nitrobenzene.
Reduce the nitro group (-NO₂) in nitrobenzene to an amino group (-NH₂) by using a reducing agent such as Sn/HCl or Fe/HCl. This forms aniline (C₆H₅NH₂).
Convert the amino group (-NH₂) in aniline to a diazonium ion (-N₂⁺) by treating it with NaNO₂ and HCl at 0–5°C. This forms benzene diazonium chloride (C₆H₅N₂⁺Cl⁻).
Perform a Sandmeyer reaction to introduce a carboxylic acid group (-COOH) at the para position relative to the diazonium group. Use CuCN followed by hydrolysis to achieve this transformation, forming para-aminobenzoic acid.
Introduce the methyl group (-CH₃) and hydroxyl group (-OH) at the appropriate positions. Use Friedel-Crafts alkylation with CH₃Cl/AlCl₃ to add the methyl group, and then perform selective hydroxylation using appropriate reagents to obtain 2-methyl-5-hydroxybenzoic acid.
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:
14mConcetti chiave
Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.
Benzene and its Derivatives
Benzene is a fundamental aromatic hydrocarbon characterized by its stable ring structure and delocalized π-electrons. Understanding benzene's reactivity is crucial, as it undergoes electrophilic substitution reactions rather than addition, allowing for the introduction of various functional groups while preserving the aromatic system.
Video consigliato:
02:49
Aromatic synthesis starting with benzene/benzene derivatives
Diazonium Ions
Diazonium ions are highly reactive intermediates formed from aromatic amines and nitrous acid. They play a pivotal role in organic synthesis, particularly in electrophilic aromatic substitution reactions, where they can be used to introduce various substituents onto the benzene ring, such as hydroxyl or carboxylic acid groups.
Video consigliato:
Percorso guidato
3:39Metal Ion Catalysis Concept 1
Functional Group Transformation
Functional group transformation involves converting one functional group into another through chemical reactions. In the context of synthesizing 2-methyl-5-hydroxybenzoic acid, understanding how to manipulate functional groups, such as converting diazonium ions into hydroxyl or carboxylic acid groups, is essential for achieving the desired product.
Video consigliato:
02:36Identifying Functional Groups
Pratica correlata
Domanda del libro di testo
Synthesize from benzene. (Hint: All of these require diazonium ions.)
(a) 3-ethylbenzoic acid
809
views
Domanda del libro di testo
Synthesize from benzene. (Hint: All of these require diazonium ions.)
(d) 4-methoxyaniline
1523
views
Domanda del libro di testo
The following drugs are synthesized using the methods in this chapter and in previous chapters. Devise a synthesis for each, starting with any compounds containing no more than six carbon atoms.
(c) Dopamine, one of the neurotransmitters in the brain. Parkinson’s disease is thought to result from a dopamine deficiency.
873
views
Domanda del libro di testo
Synthesize Novocaine from benzene and any other reagents of four carbons or fewer.
1544
views
Domanda del libro di testo
Propose mechanisms for the following reactions.
(b)
773
views