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Related Concept Videos

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Hydroboration-Oxidation of Alkenes03:08

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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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Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

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Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more...
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Oxidation of Alcohols02:37

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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Oxymercuration-Reduction of Alkenes02:36

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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
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Selective oxidation conversion of methanol/dimethyl ether.

Xiujuan Gao1,2, Junfeng Zhang1, Faen Song1

  • 1State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Science, Taiyuan 030001, China. qdzhang@sxicc.ac.cn.

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Summary

Converting methanol and dimethyl ether (DME) into valuable chemicals via selective oxidation offers a green route. This research reviews advances in synthesizing formaldehyde, methyl formate, and other products from methanol/DME.

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Area of Science:

  • Catalysis
  • Green Chemistry
  • Chemical Engineering

Background:

  • Methanol and dimethyl ether (DME) are key industrial platform chemicals with overcapacity.
  • Converting these abundant resources into higher-value products is crucial.

Purpose of the Study:

  • To review recent advancements in the selective oxidation of methanol/DME to valuable oxygenated chemicals.
  • To discuss reaction mechanisms, including molecule adsorption, bond cleavage, and chain growth.

Main Methods:

  • Selective oxidation reactions of methanol and DME.
  • Catalyst design and application analysis.
  • Mechanistic studies on reactant activation and bond cleavage.

Main Results:

  • Summarized synthesis of formaldehyde, methyl formate, dimethoxymethane, and polyoxymethylene dimethyl ethers.
  • Detailed discussion on the role of catalysts in C-O, C-H, and O-H bond activation.
  • Insights into C-O chain growth mechanisms for product formation.

Conclusions:

  • Selective oxidation of methanol/DME is a promising green pathway for high-value chemicals.
  • Catalyst design is key to controlling selectivity and efficiency.
  • Future research should focus on overcoming current challenges in catalyst development and application.