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Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

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Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

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Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
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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.
As with other organic compounds, alcohols and...
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Protection of Alcohols02:31

Protection of Alcohols

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This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
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Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems01:19

Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems

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Phase I biotransformation reactions are integral to drug metabolism, predominantly involving oxidative, reductive, and hydrolytic transformations. Chief among these are oxidative reactions, which enhance the hydrophilicity of xenobiotics and introduce polar functional groups to facilitate their elimination from the body.
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
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ANTIALGAL ACTIVITY OF SOME SIMPLE PHENOLS(1).

J McLachlan1, J S Craigie1

  • 1Atlantic Regional Laboratory, National Research Council, Halifax, Nova Scotia.

Journal of Phycology
|April 8, 2016
PubMed
Summary

Simple phenols, especially ortho dihydroxy compounds, exhibit significant antialgal activity against marine algae. Certain species like Skeletonema costatum were highly sensitive, suggesting ecological impacts.

Area of Science:

  • Marine Biology
  • Chemical Ecology
  • Phycology

Background:

  • Phenolic compounds are widely distributed in nature and can exhibit biological activity.
  • Marine algae form the base of many oceanic food webs and are sensitive to environmental changes.
  • Understanding the effects of chemical compounds on algal growth is crucial for marine ecosystem studies.

Purpose of the Study:

  • To investigate the antialgal activity of various simple phenols on seven species of unicellular marine algae.
  • To compare the toxicity of different phenolic structures (monohydroxy vs. ortho dihydroxy) and specific known algal phenols.
  • To identify the most sensitive and resistant algal species to phenolic compounds.

Main Methods:

  • Culturing seven species of unicellular marine algae.

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  • Exposing algal cultures to a range of simple phenols.
  • Measuring the effect of phenols on algal growth rates.
  • Comparing toxicity data across different phenolic compounds and algal species.

    • Main Results:

    • Known algal phenols (5-bromo-3,4-dihydroxybenzaldehyde, 2,3-dibromo-4,5-dihydroxybenzylalcohol, 3,4-dihydroxyphenylethylamine) and other ortho dihydroxy compounds demonstrated high toxicity.
    • Monohydroxy phenols exhibited significantly lower toxicity compared to ortho dihydroxy compounds.
    • Skeletonema costatum and Olisthodiscus sp. were the most sensitive algae, while Dunaliella tertiolecta was the most resistant.

    Conclusions:

    • Ortho dihydroxy phenols possess potent antialgal properties, impacting marine algal growth.
    • Algal species exhibit differential sensitivity to phenolic compounds, with implications for marine microbial ecology.
    • These findings highlight the potential ecological roles of phenolic compounds in marine environments.