Domanda del libro di testo
For each compound,
(1) classify the nitrogen-containing functional groups.
(2) provide an acceptable name.
(a)
(b)
(c)
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Ch. 19 - Amines
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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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 31d
Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene and toluene as your aromatic starting materials.
(d) m-aminobenzoic acid
Guida verificata passo dopo passo1
Step 1: Begin with the appropriate aromatic starting material. In this case, use toluene as the starting material since it contains a methyl group that can direct incoming substituents to the ortho and para positions.
Step 2: Perform an aromatic nitration reaction on toluene. Use a mixture of concentrated HNO₃ (nitric acid) and concentrated H₂SO₄ (sulfuric acid) to introduce a nitro group (-NO₂) onto the aromatic ring. The methyl group on toluene will direct the nitro group to the ortho and para positions, but you will also obtain some meta product. Separate and isolate the meta-nitrotoluene product.
Step 3: Oxidize the methyl group of meta-nitrotoluene to a carboxylic acid group (-COOH). This can be achieved using a strong oxidizing agent such as KMnO₄ (potassium permanganate) under acidic or basic conditions. The product will be m-nitrobenzoic acid.
Step 4: Reduce the nitro group (-NO₂) in m-nitrobenzoic acid to an amino group (-NH₂). This can be done using a reducing agent such as Sn (tin) and HCl (hydrochloric acid), or alternatively, catalytic hydrogenation (H₂ with a metal catalyst like Pd/C). The product will be m-aminobenzoic acid.
Step 5: Purify the final product, m-aminobenzoic acid, by recrystallization or another appropriate purification method to ensure the desired compound is obtained in high purity.
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Aromatic Nitration
Aromatic nitration is a chemical reaction that introduces a nitro group (-NO2) into an aromatic compound, typically using a mixture of concentrated nitric acid and sulfuric acid. This electrophilic substitution reaction is crucial for preparing aromatic amines, as it allows for the functionalization of the aromatic ring, which can then be further modified through reduction.
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08:19
Intro to Aromaticity
Reduction of Nitro Compounds
The reduction of nitro compounds involves converting the nitro group (-NO2) into an amine group (-NH2). This can be achieved using various reducing agents, such as iron and hydrochloric acid or catalytic hydrogenation. This step is essential for transforming the nitrated aromatic compound into the desired aromatic amine, such as m-aminobenzoic acid.
Video consigliato:
03:23Reduction of Nitro Groups
Ortho/Para vs. Meta Directing Effects
In electrophilic aromatic substitution reactions, substituents on the aromatic ring can influence the position of new substituents. Electron-donating groups, like amines, direct incoming electrophiles to the ortho and para positions, while electron-withdrawing groups, like nitro groups, direct them to the meta position. Understanding these directing effects is vital for predicting the product distribution in the synthesis of m-aminobenzoic acid.
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04:42Ortho, Para major products
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