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Related Concept Videos

Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

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Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
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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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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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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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Dynamic Equilibrium

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A reversible chemical reaction represents a chemical process that proceeds in both forward (left to right) and reverse (right to left) directions. When the rates of the forward and reverse reactions are equal, the concentrations of the reactant and product species remain constant over time and the system is at equilibrium. A special double arrow is used to emphasize the reversible nature of the reaction. The relative concentrations of reactants and products in equilibrium systems vary greatly;...
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Hemiacetal-based dynamic systems: a new mechanistic insight.

Radek Coufal1,2, Zdeněk Tošner3, Dušan Drahoňovský4

  • 1Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 8/2030, 128 40 Prague 2, Czech Republic. radek.coufal@tul.cz.

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Summary

Hemiacetal formation is best explained by an assisted proton transfer mechanism via a pseudo eight-membered transition state, aligning theory with experimental data. Other pathways, like direct proton transfer, are energetically unfavorable.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • Hemiacetal formation is a fundamental reaction in organic chemistry.
  • Understanding the reaction mechanism is crucial for synthetic applications.

Purpose of the Study:

  • To elucidate the mechanism of hemiacetal formation using pyrazine trifluoromethylketone and simple alcohols.
  • To compare theoretical calculations with experimental spectroscopic data.

Main Methods:

  • Quantum chemical calculations were employed to determine free energy profiles.
  • NMR spectroscopy was used for kinetic and thermodynamic measurements.

Main Results:

  • An assisted proton transfer via a pseudo eight-membered transition state was identified as the favored pathway.
  • A novel pathway involving a five-membered transition state leading to zwitterionic intermediates was proposed.
  • Direct proton transfer (pseudo four-membered transition state) and H-transfer via six-membered transition states were ruled out due to high energy barriers.

Conclusions:

  • The pseudo eight-membered transition state pathway accurately explains experimental observations.
  • The study provides a comprehensive mechanistic understanding of hemiacetal formation.
  • Computational and experimental approaches are complementary in mechanistic studies.