Textbook Question
Propose a mechanism for the synthesis of methyl orange.
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Ch. 19 - Amines
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 19, Problem 23d
Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.
(d) aniline
Verified step by step guidance1
Step 1: Recognize the functional group in aniline. Aniline is an aromatic amine with the structure C₆H₅NH₂, where the amino group (-NH₂) is directly attached to a benzene ring.
Step 2: Understand the reaction conditions. Sodium nitrite (NaNO₂) in dilute HCl generates nitrous acid (HNO₂) in situ. This is a key reagent for diazotization reactions, which occur with primary aromatic amines like aniline.
Step 3: Write the diazotization reaction. The amino group (-NH₂) of aniline reacts with nitrous acid (HNO₂) under acidic conditions to form a diazonium salt. The reaction can be represented as: C₆H₅NH₂ + HNO₂ + HCl → C₆H₅N₂⁺Cl⁻ + 2H₂O.
Step 4: Identify the product. The product of this reaction is benzenediazonium chloride (C₆H₅N₂⁺Cl⁻), which is a diazonium salt. This compound is highly reactive and can undergo further reactions, depending on the conditions.
Step 5: Note the importance of temperature. Diazotization reactions are typically carried out at low temperatures (0–5°C) to stabilize the diazonium salt and prevent its decomposition.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Amines
Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They can be classified as primary, secondary, or tertiary based on the number of carbon-containing groups attached to the nitrogen atom. Aniline, specifically, is a primary aromatic amine where the amino group (-NH2) is directly attached to a benzene ring.
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Reductive Amination
Diazotization
Diazotization is a chemical reaction that involves the conversion of primary amines into diazonium salts by treatment with nitrous acid (generated in situ from sodium nitrite and hydrochloric acid). This reaction is crucial in organic synthesis, particularly for the preparation of azo compounds, which are important in dye chemistry. In the case of aniline, the amino group reacts with nitrous acid to form benzenediazonium chloride.
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Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction mechanism in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. The presence of the amino group in aniline activates the benzene ring towards electrophilic attack, making it more reactive. After diazotization, the diazonium salt can undergo further reactions, such as substitution with nucleophiles, leading to various aromatic derivatives.
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Related Practice
Textbook Question
Show how you would convert aniline to the following compounds.
(a) fluorobenzene
(b) chlorobenzene
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Textbook Question
Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.
(b) N-ethylhexan-2-amine
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Textbook Question
Give the expected products of lithium aluminum hydride reduction of the following compounds (followed by hydrolysis).
(a) butyronitrile
(b) N-cyclohexylacetamide
(c) ε-caprolactam
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Textbook Question
When the (R,R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide, then heated, the major product is the Hofmann product.
(b) Some Zaitsev product is also formed. It has the (E) configuration. When the same amine is treated with mCPBA and heated, the Zaitsev product has the (Z) configuration. Use stereochemical drawings of the transition states to explain these observations.
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Textbook Question
Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.
(c) piperidine
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