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Related Concept Videos

Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

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Updated: Jun 1, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

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

Published on: August 16, 2018

2-(4-Bromo-phen-oxy)propanohydrazide.

Tashfeen Akhtar, M Khawar Rauf, Masahiro Ebihara

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

    This study details a novel chemical intermediate, C(9)H(11)BrN(2)O(2), crucial for synthesizing various heterocyclic compounds. Its crystal structure reveals specific molecular arrangements stabilized by hydrogen bonds.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Medicinal Chemistry

    Background:

    • Heterocyclic compounds are vital in pharmaceuticals and materials science.
    • Efficient synthesis of complex heterocycles requires versatile intermediates.
    • Understanding molecular structure aids in designing new synthetic routes.

    Purpose of the Study:

    • To characterize a novel intermediate, C(9)H(11)BrN(2)O(2).
    • To explore its utility in synthesizing azoles and oxadiazoles.
    • To elucidate the crystal structure and intermolecular interactions.

    Main Methods:

    • Chemical synthesis of the title compound.
    • Single-crystal X-ray diffraction analysis.
    • Analysis of dihedral angles and hydrogen bonding.

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    Main Results:

    • The compound C(9)H(11)BrN(2)O(2) was synthesized and characterized.
    • The bromo-phenoxy group exhibits a dihedral angle of 82.81° with the propanohydrazide moiety.
    • Intermolecular N-H⋯O hydrogen bonds stabilize the crystal structure, forming columns along the b axis.

    Conclusions:

    • C(9)H(11)BrN(2)O(2) is a valuable intermediate for synthesizing diverse heterocyclic compounds.
    • The determined crystal structure provides insights into molecular packing and stability.
    • This research facilitates the development of novel azole and oxadiazole derivatives.