Domanda del libro di testo
Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.
(e)
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Ch. 18 - Ketones and Aldehydes
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 18, Problema 30a
Write the sequence of steps required for the conversion of benzene into benzenediazonium chloride.
Guida verificata passo dopo passo1
Step 1: Begin with benzene (C₆H₆) as the starting material. Perform nitration of benzene by reacting it with concentrated nitric acid (HNO₃) and concentrated sulfuric acid (H₂SO₄) as a catalyst. This introduces a nitro group (-NO₂) onto the benzene ring, forming nitrobenzene (C₆H₅NO₂).
Step 2: Reduce the nitro group (-NO₂) in nitrobenzene to an amino group (-NH₂). This can be achieved by catalytic hydrogenation (using H₂ gas and a metal catalyst like Pd/C) or by chemical reduction using tin (Sn) and hydrochloric acid (HCl). The product is aniline (C₆H₅NH₂).
Step 3: Prepare a solution of sodium nitrite (NaNO₂) in water and cool it to 0-5°C. This is necessary to generate nitrous acid (HNO₂) in situ, which is unstable and decomposes at higher temperatures.
Step 4: React aniline (C₆H₅NH₂) with the freshly prepared nitrous acid (HNO₂) in the presence of hydrochloric acid (HCl) at 0-5°C. This reaction is called diazotization and results in the formation of benzenediazonium chloride (C₆H₅N₂⁺Cl⁻).
Step 5: Ensure the reaction mixture is kept cold (0-5°C) throughout the diazotization process to stabilize the benzenediazonium chloride, as it is prone to decomposition at higher temperatures.
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Electrophilic Aromatic Substitution
Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is crucial for modifying benzene derivatives, as it allows for the introduction of various functional groups. In the case of converting benzene to benzenediazonium chloride, the first step involves the nitration of benzene to form nitrobenzene, which is then further processed.
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03:07
EAS Review
Nitration of Benzene
Nitration is the process of introducing a nitro group (-NO2) into an aromatic compound, typically using a mixture of concentrated nitric acid and sulfuric acid. This reaction is an example of electrophilic aromatic substitution, where the nitronium ion (NO2+) acts as the electrophile. The formation of nitrobenzene from benzene is a critical step in the synthesis of benzenediazonium chloride, as it sets the stage for subsequent reactions.
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09:04Benzene Nomenclature
Diazotization
Diazotization is the conversion of primary aromatic amines into diazonium salts, which are highly reactive intermediates in organic synthesis. This process typically involves treating an amine with nitrous acid (generated in situ from sodium nitrite and a mineral acid) at low temperatures. For the conversion of nitrobenzene to benzenediazonium chloride, the nitro group is first reduced to an amine, which is then diazotized to form the desired diazonium compound.
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06:59Replacement Reactions
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Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide.
(b) Show how this sequence might be used to convert cis-cyclooctene to trans-cyclooctene.
526
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Domanda del libro di testo
Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.
(f)
672
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Domanda del libro di testo
Trimethylphosphine is a stronger nucleophile than triphenylphosphine, but it is rarely used to make ylides. Why is trimethylphosphine unsuitable for making most phosphorus ylides?
1192
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Domanda del libro di testo
(a) Outline the syntheses indicated in Solved Problem 18-2, beginning with aldehydes and alkyl halides.
(b) Both of these syntheses of 1-phenylbuta-1,3-diene form the central double bond. Show how you would synthesize this target molecule by forming the terminal double bond.
1530
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Domanda del libro di testo
Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide.
(a) Show each step in the reaction of trans-2,3-epoxybutane with triphenylphosphine to give but-2-ene. What is the stereochemistry of the double bond in the product?
920
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