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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

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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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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
6.2K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

11.9K
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.
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Hess's Law03:40

Hess's Law

56.4K
There are two ways to determine the amount of heat involved in a chemical change: measure it experimentally, or calculate it from other experimentally determined enthalpy changes. Some reactions are difficult, if not impossible, to investigate and make accurate measurements for experimentally. And even when a reaction is not hard to perform or measure, it is convenient to be able to determine the heat involved in a reaction without having to perform an experiment.
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.7K
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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Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
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Controllable decomposition of Ca(BH4)2 for reversible hydrogen storage.

Y Yan1, D Rentsch2, A Remhof2

  • 1Interdisciplinary Nanoscience Center (iNANO), Aarhus University, DK-8000 Aarhus C, Denmark. yigang.yan@inano.au.dk and EMPA, Swiss Federal Laboratories for Materials Science and Technology, CH-8600 Dübendorf, Switzerland.

Physical Chemistry Chemical Physics : PCCP
|March 7, 2017
PubMed
Summary

Calcium borohydride (Ca(BH4)2) can store 9.6 wt% hydrogen. This study details two methods to form calcium boride (CaB6) during Ca(BH4)2 decomposition, crucial for reversible hydrogen storage.

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Area of Science:

  • Materials Science
  • Chemical Engineering
  • Hydrogen Storage

Background:

  • Reversible hydrogen storage is critical for clean energy technologies.
  • Calcium borohydride (Ca(BH4)2) shows potential for high hydrogen storage capacity.
  • The formation of specific byproducts during dehydrogenation impacts rehydrogenation efficiency.

Purpose of the Study:

  • To investigate methods for forming calcium boride (CaB6) from Ca(BH4)2 decomposition.
  • To identify conditions favoring CaB6 formation over other boron species.
  • To optimize Ca(BH4)2 for reversible hydrogen storage.

Main Methods:

  • Experimental decomposition of Ca(BH4)2 at different temperatures.
  • Analysis of decomposition pathways and byproduct formation.
  • Characterization of solid residues to identify CaB6.

Main Results:

  • Two distinct experimental protocols for CaB6 formation were reported.
  • Decomposition below the melting point (350 °C) proceeds via CaB2H6 to yield CaB6.
  • Decomposition above the melting point (400 °C) proceeds via elemental boron to yield CaB6.

Conclusions:

  • The formation of CaB6 is essential for the reversible hydrogen storage of Ca(BH4)2.
  • Controlling decomposition temperature influences the intermediate pathway and final CaB6 product.
  • These findings provide pathways for developing efficient Ca(BH4)2-based hydrogen storage materials.