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Related Concept Videos

Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic acyl substitution.
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.
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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 acid...
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

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 eliminated to generate the benzyne...

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Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia
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Fluorous hydroformylation.

Xi Zhao1, Dongmei He, László T Mika

  • 1Department of Biology and Chemistry, City University of Hong Kong, Kowloon, Hong Kong.

Topics in Current Chemistry
|October 6, 2011
PubMed
Summary
This summary is machine-generated.

This review covers fluorous phosphine-modified catalysts used in olefin hydroformylation. These catalysts offer unique properties for efficient chemical synthesis.

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Area of Science:

  • Catalysis
  • Organometallic Chemistry
  • Green Chemistry

Background:

  • Hydroformylation is a key industrial process for producing aldehydes.
  • Traditional hydroformylation catalysts can be difficult to separate and recycle.
  • Fluorous chemistry offers novel approaches for catalyst immobilization and recovery.

Purpose of the Study:

  • To review the advancements in fluorous phosphine-modified catalysts for hydroformylation.
  • To highlight the advantages of using fluorous tags in catalyst design.
  • To discuss the scope and limitations of these catalytic systems.

Main Methods:

  • Literature review of studies employing fluorous phosphine ligands.
  • Analysis of catalyst performance in hydroformylation reactions.
  • Discussion of separation and recycling techniques for fluorous catalysts.

Main Results:

  • Fluorous phosphine-modified catalysts demonstrate high activity and selectivity in olefin hydroformylation.
  • Facilitated separation of catalysts from reaction products using fluorous phase techniques.
  • Potential for catalyst reuse, improving process economics and sustainability.

Conclusions:

  • Fluorous phosphine-modified catalysts represent a promising strategy for efficient and recyclable hydroformylation.
  • The unique properties of fluorous compounds enable simplified catalyst recovery.
  • Further development could lead to broader industrial adoption of these advanced catalytic systems.