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Related Concept Videos

Ethers to Alkyl Halides: Acidic Cleavage02:18

Ethers to Alkyl Halides: Acidic Cleavage

5.1K
Ethers are generally unreactive and unsuitable for direct nucleophilic substitution reactions since the alkoxy groups are strong bases and, therefore, poor leaving groups. However, ethers readily undergo acidic-cleavage reactions. Ethers can be converted to alkyl halides when heated with strong acids such as HBr and HI in a sequence of two substitution reactions.
5.1K
Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

2.2K
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...
2.2K
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.3K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.3K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

3.2K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the...
3.2K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.5K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.5K
Urinary Tract Calculi VI: Surgical Management01:25

Urinary Tract Calculi VI: Surgical Management

1.0K
Procedures for Kidney StonesMedical intervention is necessary when kidney stones or renal calculi are too large to pass spontaneously (typically greater than 5 millimeters) when stones are accompanied by symptomatic infection (such as fever or pyelonephritis), when they impair kidney function, or when they cause persistent symptoms like severe pain, nausea, or urinary retention. Additionally, patients with only one kidney or those who cannot be treated with medical management also require...
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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
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Cholelitholysis using methyl tertiary butyl ether.

M J Allen, T J Borody, T F Bugliosi

    Gastroenterology
    |January 1, 1985
    PubMed
    Summary
    This summary is machine-generated.

    Methyl tertiary-butyl ether effectively dissolves cholesterol gallstones in vitro and in vivo. This potential solvent shows rapid efficacy and good tolerance, warranting further study for human gallbladder and bile duct stones.

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    Area of Science:

    • Biochemistry
    • Pharmacology

    Background:

    • Gallstones are a common ailment, with cholesterol stones being the most prevalent type.
    • Current treatments for cholesterol gallstones have limitations, necessitating the development of effective dissolution agents.

    Purpose of the Study:

    • To evaluate the efficacy of methyl tertiary-butyl ether (MTBE) as a solvent for cholesterol gallstones.
    • To assess the safety and tolerance of MTBE for direct instillation into the gallbladder or bile duct.

    Main Methods:

    • In vitro dissolution assays using human gallstones with varying cholesterol content.
    • In vivo studies involving direct catheter instillation of MTBE into the gallbladders of 6 dogs with surgically implanted gallstones.

    Main Results:

    • MTBE rapidly dissolved human gallstones (40%-94% cholesterol) within 60-100 minutes in vitro, significantly faster than monooctanoin.
    • In dogs, MTBE dissolved implanted gallstones within 4-16 hours with only minor adverse effects observed.
    • MTBE demonstrated a favorable safety profile in vivo, with minimal clinical, biochemical, or histologic impact.

    Conclusions:

    • MTBE exhibits potent cholesterol-solubilizing properties and rapid gallstone dissolution capabilities.
    • The compound is well-tolerated in an in vivo model, suggesting potential for therapeutic use.
    • Further investigation of MTBE for the treatment of human gallbladder and biliary duct cholesterol stones is recommended.