Related Experiment Video

Updated: May 27, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

(E)-Methyl N'-[(1H-indol-3-yl)methyl-idene]hydrazinecarboxyl-ate 0.25-hydrate

Lu-Ping Lv, Tie-Ming Yu, Wen-Bo Yu

    Acta Crystallographica. Section E, Structure Reports Online
    |November 18, 2011
    PubMed

    More Related Videos

    A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species08:12

    A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

    Published on: August 16, 2018

    Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry09:37

    Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

    Published on: October 18, 2019

    Related Concept Videos

    Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

    Carboxylic Acids to Methylesters: Alkylation using Diazomethane

    Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
    Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

    Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

    Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
    Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

    Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

    Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
    Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

    Aldehydes and Ketones with Amines: Imine Formation Mechanism

    Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
    Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
    If the pH is low or the solution is too acidic, the reaction slows down in the...
    Diazonium Group Substitution: –OH and –H01:19

    Diazonium Group Substitution: –OH and –H

    Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
    Nitriles to Amines: LiAlH4 Reduction00:55

    Nitriles to Amines: LiAlH4 Reduction

    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...