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Related Concept Videos

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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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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Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group.  The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2,  depending on the nature of carbon attached to the halide.
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In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
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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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Acid-Catalyzed Aldol Addition Reaction01:15

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The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
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Updated: Aug 28, 2025

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Direct Observation of Solvent-Reaction Intermediate Interactions in Heterogeneously Catalyzed Alcohol Coupling.

Eri Muramoto1, Dipna A Patel2, Wei Chen3,4

  • 1John A. Paulson School of Engineering and Applied Sciences, Harvard University, Cambridge, Massachusetts 02138, United States.

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|September 16, 2022
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Interactions between reaction intermediates and coadsorbed methanol stabilize the catalytic surface, influencing reaction rates and selectivity. This study reveals new insights into surface chemistry for catalysis.

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Area of Science:

  • Surface Chemistry
  • Catalysis
  • Chemical Kinetics

Background:

  • Surface interactions govern catalytic reaction rates and selectivity.
  • Secondary interactions, like van der Waals forces, influence selectivity in coupling reactions.
  • Understanding intermediate-reactant interactions is crucial for surface catalysis.

Purpose of the Study:

  • To directly demonstrate the effect of interactions between adsorbed reaction intermediates and reactant molecules on binding energy and molecular arrangement.
  • To investigate the oxidative coupling reaction of methanol on a gold (Au(110)) surface.
  • To elucidate the role of methoxy intermediates in stabilizing coadsorbed methanol.

Main Methods:

  • Direct molecular-scale imaging using scanning tunneling microscopy (STM).
  • Density Functional Theory (DFT) calculations.
  • Kinetic modeling for microkinetic analysis.

Main Results:

  • Interactions between methoxy intermediates and coadsorbed methanol increase binding energy.
  • A hydrogen-bonded network formed by methoxy and methanol is stabilized by at least 0.13 eV per methanol molecule.
  • Methoxy intermediates stabilize excess adsorbed methanol, leading to desorption via beta-hydride decomposition.

Conclusions:

  • Interactions between reaction intermediates and coadsorbed species significantly impact surface chemistry.
  • Accurate kinetic models must include these interactions for predicting catalytic rates and selectivity.
  • Findings are relevant for both gas and liquid-phase catalytic reactions with significant coadsorbed species.