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Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

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Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.       
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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
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Cationic Chain-Growth Polymerization: Mechanism00:57

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
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Internal Catalysis in Dynamic Hydrogels with Associative Thioester Cross-Links.

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This study introduces bifunctional aromatic thioesters as dynamic cross-links in hydrogels. These thioesters enable tunable stress relaxation at physiological pH through accelerated transthioesterification, driven by intramolecular hydrogen bonding.

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Area of Science:

  • Biochemistry
  • Polymer Chemistry
  • Materials Science

Background:

  • Thioesters are crucial in biosynthesis and are utilized as reactive handles in chemical biology.
  • Thioester exchange reactions typically require catalysts or high pH conditions for acceleration.

Purpose of the Study:

  • To investigate the use of bifunctional aromatic thioesters as dynamic covalent cross-links in hydrogel networks.
  • To understand the mechanism and kinetics of thioester exchange at physiological pH in aqueous environments.

Main Methods:

  • Synthesis and characterization of bifunctional aromatic thioesters.
  • Fabrication and mechanical testing of hydrogels cross-linked with these thioesters.
  • Kinetic studies of transthioesterification and macromolecular stress relaxation measurements.

Main Results:

  • Demonstrated that transthioesterification occurs at physiological pH in aqueous conditions, facilitating stress relaxation within hundreds of seconds.
  • Identified intramolecular hydrogen bonding as the key factor accelerating thioester exchange.
  • Showcased tunable stress relaxation properties in hydrogels without compromising network stiffness.

Conclusions:

  • Bifunctional aromatic thioesters can serve as effective dynamic covalent cross-links in hydrogels.
  • Intramolecular hydrogen bonding significantly accelerates thioester exchange, enabling dynamic network behavior.
  • This system offers a pathway to engineer materials with adaptable mechanical properties through associative dynamic cross-links.