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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.

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

Hydrolysis of Chlorobenzene to Phenol: Dow Process

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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...

Diazonium Group Substitution: –OH and –H

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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.

Nucleophilic Aromatic Substitution: Elimination–Addition

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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...

Electrophilic Addition to Alkynes: Hydrohalogenation

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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

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Related Experiment Video

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(E)-N'-[1-(4-Bromo-phen-yl)ethyl-idene]-2-hydroxy-benzohydrazide.

Chuan-Gang Fan¹, Ming-Zhi Song

¹College of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a bromine-containing organic compound. Molecular conformation is influenced by intramolecular hydrogen bonds, and crystal packing involves intermolecular hydrogen bonds and pi-pi interactions.

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Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

Understanding molecular interactions is crucial in organic chemistry.
Crystal packing dictates material properties.
Hydrogen bonds and pi-pi interactions are key non-covalent forces.

Purpose of the Study:

To elucidate the crystal structure of the title compound C(15)H(13)BrN(2)O(2).
To analyze the role of intramolecular and intermolecular interactions in molecular conformation and crystal packing.

Main Methods:

Single-crystal X-ray diffraction was used to determine the molecular and crystal structure.
Analysis of bond lengths, bond angles, and intermolecular distances.
Identification of hydrogen bonding and pi-pi stacking interactions.

Main Results:

The compound exhibits a dihedral angle of 7.9(1)° between its two aromatic rings.
An intramolecular N-H⋯O hydrogen bond influences molecular conformation.
Intermolecular O-H⋯O hydrogen bonds form chains, and pi-pi interactions create centrosymmetric dimers.

Conclusions:

The crystal structure is stabilized by a combination of intramolecular hydrogen bonding, intermolecular hydrogen bonding, and pi-pi interactions.
These interactions dictate the overall molecular conformation and the arrangement of molecules in the crystal lattice.
The findings contribute to the understanding of structure-property relationships in organic crystalline materials.