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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
5.1K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

12.0K
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.
12.0K
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

5.2K
Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...
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Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

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Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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Oxidation of Alcohols02:37

Oxidation of Alcohols

17.5K
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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Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
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pH Responsive and Oxidation Resistant Wet Adhesive based on Reversible Catechol-Boronate Complexation.

Ameya R Narkar1, Brett Barker1, Matthew Clisch1

  • 1Department of Biomedical Engineering, Michigan Technological University , 1400 Townsend Drive, Houghton, Michigan 49931, United States.

Chemistry of Materials : a Publication of the American Chemical Society
|August 24, 2016
PubMed
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Researchers developed a pH-responsive smart adhesive using dopamine methacrylamide (DMA) and 3-acrylamido phenylboronic acid (AAPBA). This adhesive reversibly switches between adhesive and non-adhesive states, offering tunable wet adhesion for advanced applications.

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Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Surface Science

Background:

  • Developing adhesives that function effectively on wet surfaces remains a significant challenge in materials science.
  • Controlling adhesive properties through external stimuli, such as pH, is crucial for smart material applications.

Purpose of the Study:

  • To create a novel smart adhesive capable of reversible adhesion to wetted surfaces.
  • To investigate the pH-dependent adhesive and cohesive properties of a copolymer based on dopamine methacrylamide (DMA) and 3-acrylamido phenylboronic acid (AAPBA).

Main Methods:

  • Copolymerization of DMA and AAPBA to form the smart adhesive.
  • Fourier-transform infrared (FTIR) spectroscopy to confirm catechol-boronate complex formation.
  • Mechanical testing, including loss modulus measurements and Johnson Kendall Roberts (JKR) contact mechanics, to evaluate adhesion and viscoelastic properties at different pH values.

Main Results:

  • The copolymer demonstrated pH-dependent reversible complexation between catechol and boronate groups, confirmed by FTIR.
  • Adhesive cross-linking density and loss modulus significantly increased at pH 9 due to complexation, enhancing viscous dissipation.
  • The adhesive exhibited strong binding to wetted glass (work of adhesion, W_adh = 2000 mJ/m²) at pH 3, decreasing by over an order of magnitude at pH 9, demonstrating tunable wet adhesion.

Conclusions:

  • The combined DMA and AAPBA copolymer forms a smart adhesive with tunable and reversible adhesion properties.
  • The pH-triggered catechol-boronate complexation is key to modulating the adhesive network's properties and performance.
  • This smart adhesive shows potential for applications requiring reversible bonding on wet surfaces.