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Ketone synthesis by oxidation of alcohols - Organic …

T1 - Synthesis of α- and β-branched ethers from alcohols by reaction of acetals with Grignard reagents

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Synthesis of ketones by oxidation of alcohols

Synthesis of Alcohols
Alkenes react with water, in the presence of acid, to yield alcohols. The mechanism follows Markovnikov addition. Alkyl halides react with hydroxide to produce alcohols. Organolithium or Grignard reagents add to aldehydes and ketones to produce alcohols. Hydrogen, from sodium borohydride, lithium aluminum hydride, or hydrogen, adds to aldehydes and ketones to produce alcohols.

Stereodivergent Synthesis of the Diamino Alcohol Core of Ritonavir and Its C-2 Epimer

Synthesis and Reactions of Ethers
In the Williamson ether synthesis, alkoxide ions react with zero degree or primary alkyl halides to form ethers. Ethers are cleaved with hydrogen halides to form alkyl halides and alcohols. The alkyl group in the alkyl halide is the least hindered alkyl group in the ether.

Williamson ether synthesis (video) | Khan Academy

Synthesis of Alcohols

Synthesis of Alcohols
Alkenes react with water, in the presence of acid, to yield alcohols. The mechanism follows Markovnikov addition. Alkyl halides react with hydroxide to produce alcohols. Organolithium or Grignard reagents add to aldehydes and ketones to produce alcohols. Hydrogen, from sodium borohydride, lithium aluminum hydride, or hydrogen, adds to aldehydes and ketones to produce alcohols.

Reactions of Alcohols
Alkoxide ions are formed from the reaction of alcohols with metal. Alcohols react with hydrogen halide, phosphorus trihalide, or thionyl chloride to form alkyl halides. Alcohols are dehydrated with acid and heat to form alkenes. Zero degree and primary alcohols are oxidized with pyridinium chlorochromate to form aldehydes. Zero degree and primary alcohols are oxidized with sodium dichromate, potassium dichromate, potassium permanganate, sodium hypochlorite, nitric acid, or chromium trioxide to form carboxylic acids. Secondary alcohols are oxidized with sodium dichromate, potassium dichromate, potassium permanganate, sodium hypochlorite, nitric acid, chromium trioxide, or pyridinium chlorochromate to ketones. Tertiary alcohols are not oxidized with sodium dichromate, potassium dichromate, potassium permanganate, sodium hypochlorite, nitric acid, chromium trioxide, or pyridinium chlorochromate. Alcohols react with carboxylic acids, in the presence of acid, to yield esters.

Nickel-catalyzed direct synthesis of dialkoxymethane ethers

AB - Non-symmetrical acetals have been combined with Grignard reagents in toluene at reflux to generate α-and β-branched ethers in moderate to high yields. The synthesis of isopropyl and isobutyl ethers of the bicyclic alcohol 1 was accomplished using this methodology, although reactions in the synseries were complicated by the formation of tricyclic products by an intramolecular cyclisation. The scope and limitations of the ether-forming reactions were explored with a series of acetals derived from primary, secondary and tertiary alcohols. The halide component of the Grignard reagent and the solvent were found to be an important factor in facilitating these reactions.

AB - Non-symmetrical acetals have been combined with Grignard reagents in toluene at reflux to generate α-and β-branched ethers in moderate to high yields. The synthesis of isopropyl and isobutyl ethers of the bicyclic alcohol 1 was accomplished using this methodology, although reactions in the synseries were complicated by the formation of tricyclic products by an intramolecular cyclisation. The scope and limitations of the ether-forming reactions were explored with a series of acetals derived from primary, secondary and tertiary alcohols. The halide component of the Grignard reagent and the solvent were found to be an important factor in facilitating these reactions.

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  • This reaction is called the Williamson ether synthesis

    T1 - Synthesis of α- and β-branched ethers from alcohols by reaction of acetals with Grignard reagents

  • Williamson Ether Synthesis | MendelSet

    Synthesis of Alcohols

  • This two-step process is called the Williamson ether synthesis.

    There are two primary reactions to generate ethers: either by Dehydration of Alcohols or by the Williamson Synthesis

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Synthesis of Ethers - Chemistry LibreTexts

N2 - Non-symmetrical acetals have been combined with Grignard reagents in toluene at reflux to generate α-and β-branched ethers in moderate to high yields. The synthesis of isopropyl and isobutyl ethers of the bicyclic alcohol 1 was accomplished using this methodology, although reactions in the synseries were complicated by the formation of tricyclic products by an intramolecular cyclisation. The scope and limitations of the ether-forming reactions were explored with a series of acetals derived from primary, secondary and tertiary alcohols. The halide component of the Grignard reagent and the solvent were found to be an important factor in facilitating these reactions.

Synthesis of ethers - Organic chemistry

N2 - Non-symmetrical acetals have been combined with Grignard reagents in toluene at reflux to generate α-and β-branched ethers in moderate to high yields. The synthesis of isopropyl and isobutyl ethers of the bicyclic alcohol 1 was accomplished using this methodology, although reactions in the synseries were complicated by the formation of tricyclic products by an intramolecular cyclisation. The scope and limitations of the ether-forming reactions were explored with a series of acetals derived from primary, secondary and tertiary alcohols. The halide component of the Grignard reagent and the solvent were found to be an important factor in facilitating these reactions.

Organic Chemistry: Alcohols and Ethers

Non-symmetrical acetals have been combined with Grignard reagents in toluene at reflux to generate α-and β-branched ethers in moderate to high yields. The synthesis of isopropyl and isobutyl ethers of the bicyclic alcohol 1 was accomplished using this methodology, although reactions in the synseries were complicated by the formation of tricyclic products by an intramolecular cyclisation. The scope and limitations of the ether-forming reactions were explored with a series of acetals derived from primary, secondary and tertiary alcohols. The halide component of the Grignard reagent and the solvent were found to be an important factor in facilitating these reactions.

Organic Chemistry/Alcohols - Wikibooks, open books …

Reactions of Alcohols
Alkoxide ions are formed from the reaction of alcohols with metal. Alcohols react with hydrogen halide, phosphorus trihalide, or thionyl chloride to form alkyl halides. Alcohols are dehydrated with acid and heat to form alkenes. Zero degree and primary alcohols are oxidized with pyridinium chlorochromate to form aldehydes. Zero degree and primary alcohols are oxidized with sodium dichromate, potassium dichromate, potassium permanganate, sodium hypochlorite, nitric acid, or chromium trioxide to form carboxylic acids. Secondary alcohols are oxidized with sodium dichromate, potassium dichromate, potassium permanganate, sodium hypochlorite, nitric acid, chromium trioxide, or pyridinium chlorochromate to ketones. Tertiary alcohols are not oxidized with sodium dichromate, potassium dichromate, potassium permanganate, sodium hypochlorite, nitric acid, chromium trioxide, or pyridinium chlorochromate. Alcohols react with carboxylic acids, in the presence of acid, to yield esters.

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