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Formation of Halohydrin from Alkenes

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.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

Diazonium Group Substitution: –OH and –H

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.

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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

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.

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Related Experiment Video

Updated: Jun 1, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

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(E)-N'-(5-Bromo-2-methoxy-benzyl-idene)-4-methoxy-benzohydrazide.

Hong-Yan Ban, Cong-Ming Li

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a novel benzohydrazide compound. The molecule exhibits a non-planar benzohydrazide group and forms hydrogen-bonded chains in its solid state.

Area of Science:

Crystallography
Organic Chemistry
Molecular Structure

Background:

Benzohydrazide derivatives are important scaffolds in medicinal chemistry.
Understanding the solid-state structure is crucial for drug design and material science.

Purpose of the Study:

To elucidate the three-dimensional molecular and crystal structure of the title compound, C(16)H(15)BrN(2)O(3).
To investigate the intermolecular interactions governing the crystal packing.

Main Methods:

Single-crystal X-ray diffraction analysis was employed.
The crystal structure was solved and refined to determine atomic positions and bonding.

Main Results:

The benzohydrazide moiety was found to be non-planar, adopting a trans configuration around the methylidene unit.

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A significant dihedral angle of 75.6(2)° was observed between the two substituted benzene rings.

Intermolecular N-H⋯O hydrogen bonds between carbonyl and amine groups resulted in the formation of chains along the c cell axis.

Conclusions:

The study provides a detailed structural characterization of the title benzohydrazide compound.
The identified hydrogen bonding network offers insights into the supramolecular assembly and potential for crystal engineering.