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Related Concept Videos

Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

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Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
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Aromatic Compounds: Overview01:25

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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
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Nomenclature of Aromatic Compounds with a Single Substituent01:23

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Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
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Benzene to Phenol via Cumene: Hock Process01:27

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The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
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Preparation of Diols and Pinacol Rearrangement01:57

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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
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Related Experiment Video

Updated: Dec 11, 2025

Quantitative 31P NMR Analysis of Lignins and Tannins
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Naphthalene Structures Derived from Lignins During Phenolation.

Suxiang Li1, Lanlan Shi1, Chen Wang1

  • 1State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou, 510640, P. R. China.

Chemsuschem
|August 20, 2020
PubMed
Summary
This summary is machine-generated.

Phenolation of lignin models reveals new naphthalene products from resinol structures. This acid-catalyzed process cleaves C1-Cα bonds, yielding valuable compounds for lignin applications.

Keywords:
NMR spectroscopyalkali lignincondensationstructure elucidationsyringaresinol

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Area of Science:

  • Wood Chemistry
  • Polymer Science
  • Organic Chemistry

Background:

  • Lignin modification enhances its reactivity for diverse industrial applications.
  • Phenolation is a key chemical treatment for activating lignin.
  • Resinol (β-β) structures are significant linkages in certain lignin types.

Purpose of the Study:

  • To investigate products derived from resinol (β-β) lignin structures under acid-catalyzed phenolation.
  • To identify novel compounds formed during the phenolation of specific lignin models.
  • To understand the reaction pathways and structural changes in lignin during phenolation.

Main Methods:

  • Acid-catalyzed phenolation of resinol lignin models (syringaresinol, pinoresinol) and eucalyptus alkali lignin.
  • Separation of phenolation products using flash chromatography and thin-layer chromatography.
  • Characterization of products via Gas Chromatography-Mass Spectrometry (GC-MS) and Nuclear Magnetic Resonance (NMR) spectroscopy, including HSQC NMR.

Main Results:

  • Identification of new naphthalene products from syringaresinol phenolation, with guaiacyl analogs also detected.
  • Cleavage of the C1-Cα bond in resinol compounds, releasing syringol or guaiacol.
  • Formation of diphenylmethane products from phenol and/or lignin-derived phenols.
  • Syringaresinol yielded more naphthalene products than pinoresinol.
  • HSQC NMR confirmed the presence of naphthalene structures in phenolated alkali lignin.

Conclusions:

  • Acid-catalyzed phenolation effectively transforms resinol lignin structures into naphthalene derivatives.
  • The study elucidates specific reaction pathways involving C1-Cα bond cleavage and subsequent cyclization.
  • Phenolation offers a viable route to functionalize lignin, generating novel chemical entities from specific structural units.