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Related Concept Videos

Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

16.2K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
3.0K
Characteristics and Nomenclature of Homopolymers01:00

Characteristics and Nomenclature of Homopolymers

3.2K
Polymers that are made up of identical monomer units are called homopolymers. Only one repeating unit is involved in the construction of the homopolymer structure. For example, as depicted in Figure 1, polypropylene is a homopolymer constituted of propylene monomers. Here, the only repeating unit in the polymer chain is propylene.
3.2K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.9K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
2.9K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

18.8K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
18.8K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

8.2K
Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
8.2K

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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HFIP in Organic Synthesis.

Hashim F Motiwala1, Ahlam M Armaly1, Jackson G Cacioppo1

  • 1Divison of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599 United States.

Chemical Reviews
|July 18, 2022
PubMed
Summary
This summary is machine-generated.

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a versatile polar solvent increasingly used in organic synthesis. Its unique properties stabilize reactions, making it ideal for C-H functionalization and other transformations.

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry

Background:

  • 1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar solvent with strong hydrogen-bonding capabilities.
  • Its use in organic synthesis has grown significantly due to its ability to stabilize ionic species and facilitate intermolecular interactions.

Purpose of the Study:

  • To review the applications of HFIP in organic synthesis.
  • To highlight the impact of HFIP on various organic reactions.

Main Methods:

  • Literature review of organic reactions utilizing HFIP.
  • Analysis of HFIP's physical properties and their influence on reaction outcomes.

Main Results:

  • HFIP stabilizes ionic intermediates and facilitates proton transfer.
  • HFIP has become a preferred solvent in areas like C-H functionalization chemistry.
  • Examples demonstrate HFIP's positive effect as a solvent or additive in diverse organic reactions.

Conclusions:

  • HFIP is a valuable and increasingly important solvent in modern organic synthesis.
  • Its unique properties offer significant advantages for a wide range of chemical transformations.