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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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.

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.

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

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.

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.

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.

Alkyl Halides

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

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Updated: Jun 1, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

N'-[(1E)-1-(4-Chloro-phen-yl)ethyl-idene]formohydrazide.

Zahid Shafiq, Muhammad Yaqub, M Nawaz Tahir

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study reveals that the crystal structure of C(9)H(9)ClN(2)O features centrosymmetric dimers linked by intermolecular hydrogen bonds. These bonds form specific ring motifs, influencing the molecule's overall arrangement.

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Last Updated: Jun 1, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

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Published on: August 22, 2018

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

Area of Science:

Crystallography
Molecular Structure
Supramolecular Chemistry

Background:

Understanding the intermolecular interactions in organic compounds is crucial for predicting their bulk properties.
Crystal structure analysis provides detailed insights into molecular arrangement and bonding.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(9)H(9)ClN(2)O.
To characterize the intermolecular interactions and resulting supramolecular architecture.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
Analysis of hydrogen bonding and dihedral angles was performed.

Main Results:

The compound forms centrosymmetric dimers through intermolecular N-H⋯O hydrogen bonds.
These interactions result in the formation of R(2)(2)(8) ring motifs.
A small dihedral angle of 6.77(17)° was observed between the p-chloro-phenyl unit and the rest of the molecule.

Conclusions:

The crystal packing is dominated by intermolecular hydrogen bonding, leading to dimer formation.
The observed R(2)(2)(8) ring motif is a key feature of the supramolecular assembly.
The dihedral angle indicates a nearly planar arrangement of the core structure.