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Preparation of Nitriles01:12

Preparation of Nitriles

2.0K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.0K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.2K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
4.2K
Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

4.0K
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...
4.0K
Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

4.1K
Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
4.1K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.6K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
3.6K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.5K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.5K

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Deville rebooted - practical N2O5 synthesis.

Lee E Edwards1, Benson M Kariuki1, Matthew Didsbury2

  • 1Cardiff University, School of Chemistry, Cardiff, CF10 3AT, UK. wirth@cf.ac.uk.

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Summary
This summary is machine-generated.

Researchers optimized a 170-year-old method for synthesizing dinitrogen pentoxide (N2O5). The new photocatalytic approach offers a safe, clean, and reproducible way to produce N2O5 in high yields, with potential for industrial scale-up.

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Area of Science:

  • Inorganic chemistry
  • Chemical synthesis
  • Photocatalysis

Background:

  • Dinitrogen pentoxide (N2O5) is the anhydride of nitric acid.
  • The original synthesis method by Henri Étienne Sainte-Claire Deville (1849) involved silver nitrate and chlorine gas.
  • Deville's method had limitations in safety, reproducibility, and practicality.

Purpose of the Study:

  • To revisit, optimize, and modify Deville's N2O5 synthesis method.
  • To develop a safe, clean, practical, and reproducible alternative for N2O5 production.
  • To assess the potential for industrial scale-up of the modified method.

Main Methods:

  • Modification of Deville's original synthesis of N2O5.
  • Application of photocatalysis to the synthesis process.
  • Quantitative yield analysis and assessment of by-product recycling.

Main Results:

  • Achieved quantitative yields of N2O5.
  • Demonstrated a safe, clean, and reproducible synthesis protocol.
  • Identified silver chloride as a recyclable by-product.

Conclusions:

  • The optimized photocatalytic method provides a superior alternative to Deville's original N2O5 synthesis.
  • The modified method is suitable for safe, efficient, and reproducible N2O5 production.
  • Industrial scale-up is feasible with efficient recycling of silver chloride.