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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

10.8K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
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Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

3.1K
Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
3.1K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.8K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
3.8K
Carboxylic Acids to Primary Alcohols: Hydride Reduction01:17

Carboxylic Acids to Primary Alcohols: Hydride Reduction

3.4K
Carboxylic acids, upon reaction with strong reducing agents such as lithium aluminum hydride followed by hydrolysis, undergo reduction to form primary alcohols.
3.4K
Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids01:24

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

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Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...
3.7K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.9K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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Updated: Sep 14, 2025

Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase
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Formic Acid Electroreduction Pathways on (111) Metal Surfaces.

Zhe Meng1, Henrik H Kristoffersen1, Jan Rossmeisl1

  • 1Department of Chemistry, University of Copenhagen, Universitetsparken 5, Copenhagen, 2100, Denmark.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|July 19, 2025
PubMed
Summary
This summary is machine-generated.

Formic acid electroreduction on various metal surfaces was studied. Gold (Au) shows promise for methanol production, while copper (Cu) offers varied products, and platinum group metals risk catalyst poisoning.

Keywords:
(111) facetscatalystselectroreductionformic acidmetal surfaces

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Area of Science:

  • Electrochemistry
  • Materials Science
  • Catalysis

Background:

  • Formic acid electroreduction is an understudied area with potential for energy applications.
  • Understanding reaction pathways and product selectivity is crucial for catalyst development.

Purpose of the Study:

  • Investigate formic acid electroreduction on Cu(111), Au(111), Ag(111), Zn(111), Pt(111), Pd(111), and Ru(111).
  • Determine the most likely products and assess catalyst selectivity using theoretical calculations.

Main Methods:

  • Density functional theory (DFT) calculations were employed.
  • Analysis of four formic acid electroreduction steps on specified metal surfaces.

Main Results:

  • Copper (Cu) surfaces allow formation of H2, CO, C2 products, methanol, and methane, but exhibit low selectivity.
  • Gold (Au) surfaces show high selectivity for methanol with low hydrogen evolution.
  • Silver (Ag) may produce methanol but has a high initial energy barrier; Zinc (Zn) favors methane; Platinum (Pt), Palladium (Pd), and Ruthenium (Ru) risk CO poisoning.

Conclusions:

  • Gold (Au) emerges as a promising catalyst for selective methanol production.
  • Understanding intermediate adsorption and reaction pathways is key to optimizing formic acid electroreduction.
  • DFT provides valuable insights into catalyst performance for energy conversion applications.