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Related Concept Videos

Conversion of Alcohols to Alkyl Halides02:48

Conversion of Alcohols to Alkyl Halides

This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
Preparation of Alcohols via Substitution Reactions01:38

Preparation of Alcohols via Substitution Reactions

Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
Protection of Alcohols02:31

Protection of Alcohols

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...
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Selective Electrochemical Defluorinative Hydroxymethylation toward Difluoro-Substituted Alcohol Building Blocks.

Andrey Shatskiy1, Márk Holczer1, Johannes Winter1

  • 1Department of Chemistry, KTH Royal Institute of Technology, SE-100 44 Stockholm, Sweden.

Organic Letters
|June 2, 2026
PubMed
Summary

This study introduces a novel electrochemical method for synthesizing difluoromethyl compounds, crucial for pharmaceuticals and agrochemicals. The process efficiently converts trifluoromethyl arenes into valuable difluoromethylated alcohol building blocks.

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups
06:44

Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups

Published on: April 6, 2017

Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Fluorine Chemistry

Background:

  • Difluoromethylated compounds are vital in pharmaceuticals and agrochemicals.
  • Existing synthetic methods for these compounds are limited.
  • Access to difluoromethylated structures is challenging.

Purpose of the Study:

  • To develop a straightforward electrochemical synthesis for difluoromethyl-substituted alcohol building blocks.
  • To enable selective monodefluorination of trifluoromethyl arenes.
  • To provide a reliable method for accessing important fluorinated compounds.

Main Methods:

  • Electrochemical synthesis.
  • Selective monodefluorination of trifluoromethyl arenes.
  • Hydroxymethylation of arene substrates.

Main Results:

  • A straightforward electrochemical synthesis was achieved.
  • High chemoselectivity was observed for various trifluoromethyl arene substrates.
  • Mild reaction conditions were employed.
  • Mechanistic studies indicated a reductive radical-polar crossover pathway.

Conclusions:

  • The developed electrochemical method provides efficient access to difluoromethylated alcohol building blocks.
  • The synthesis is selective and proceeds under mild conditions.
  • This work offers a valuable new synthetic route for important fluorinated compounds.