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Phenol is synthesized from cumene via the scheme shown. Suggest the mechanism for each step of the reaction shown. [The oxygens have been screened in blue and orange to assist you.]
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Ch. 24 - Benzene 2: Reactions Influenced by the Aromatic Ring
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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TOC.tableOfContents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases/Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Non è quello che usi tu?Cambia libro di testo
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Mullins 1st EditionCh. 24 - Benzene 2: Reactions Influenced by the Aromatic RingProblema 66
Mullins 1st EditionCh. 24 - Benzene 2: Reactions Influenced by the Aromatic RingProblema 66Capitolo 23, Problema 66
Synthesize the dye shown starting with aniline and naphthol using reactions from Chapters 23 and 24. [Hint. Start by identifying how each substituent might be installed and then plan the order of their introduction.]
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Identify the functional groups in the target dye molecule: a carboxylate group, a sulfonate group, and an azo linkage. The starting materials are aniline and naphthol.
Begin with the diazotization of aniline. Convert the amino group of aniline to a diazonium salt by treating it with nitrous acid (HNO2) in the presence of hydrochloric acid (HCl). This forms the diazonium ion, which is a key intermediate for azo coupling.
Perform azo coupling between the diazonium salt and naphthol. The naphthol acts as a nucleophile and attacks the diazonium ion, forming the azo linkage (N=N) between the two aromatic rings.
Introduce the sulfonate group by sulfonation of the aromatic ring. This can be achieved by treating the azo compound with sulfuric acid (H2SO4) to install the sulfonate group (SO3-) on the aromatic ring.
Finally, introduce the carboxylate group by carboxylation. This can be done by treating the naphthol moiety with carbon dioxide (CO2) under basic conditions to form the carboxylate group (COO-), which can then be neutralized with calcium ions (Ca2+) to form the calcium salt.
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Amino Group Reactivity
The amino group (-NH2) in aniline is a strong nucleophile, making it highly reactive in electrophilic aromatic substitution reactions. Understanding how to introduce substituents onto the aromatic ring of aniline is crucial, as the amino group can direct new substituents to ortho and para positions, influencing the overall structure of the final dye.
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Standard Amino Acids
Naphthol Chemistry
Naphthol, which contains a hydroxyl group (-OH) on a naphthalene ring, can participate in various reactions, including electrophilic substitutions and coupling reactions. The position of the hydroxyl group affects its reactivity and the types of reactions it can undergo, making it essential to consider when planning the synthesis of the dye.
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00:28Introduction to General Chemistry Review
Dye Formation Mechanism
The synthesis of dyes often involves coupling reactions between aromatic amines and phenolic compounds. Understanding the mechanism of these reactions, including the formation of azo bonds and the role of catalysts or conditions, is vital for successfully synthesizing the desired dye structure from aniline and naphthol.
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02:26Formation of Enolates