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01:32Aldehydes 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.
01:10Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
02:41Formation 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.
01:01Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation
Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt condensation is...
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt condensation is...
01:11Nucleophilic 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...
01:20Electrophilic Aromatic Substitution: Nitration of Benzene
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Updated: Jun 5, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2-Bromo-benzaldehyde cyano-hydrin.
Richard Betz1, Franziska Betzler, Peter Klüfers
1Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13, 81377 München, Germany.
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
The crystal structure of (2-bromo-phenyl)-(hydroxy)acetonitrile reveals normal bond parameters. Molecules form extended hydrogen-bonded chains through intermolecular interactions between hydroxyl groups and nitrile nitrogen atoms.
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Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- The synthesis and structural characterization of organic compounds are fundamental to understanding chemical properties.
- Hydrogen bonding plays a crucial role in determining the solid-state architecture and physical properties of molecules.
- Nitrile groups and hydroxyl groups are common functional groups involved in various intermolecular interactions.
Purpose of the Study:
- To elucidate the crystal structure of the reaction product of 2-bromo-benzaldehyde and hydrogen cyanide, identified as (2-bromo-phenyl)-(hydroxy)acetonitrile.
- To investigate the nature of intermolecular interactions within the crystal lattice.
- To analyze the hydrogen bonding network and its influence on molecular arrangement.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
- Analysis of bond lengths, bond angles, and intermolecular contacts was performed.
- Hydrogen bond geometry, including donor-acceptor distances and angles, was examined.
Main Results:
- The title compound, C(8)H(6)BrNO, was successfully synthesized and its crystal structure determined.
- Bond lengths and angles were found to be within expected ranges, indicating normal molecular geometry.
- An intermolecular hydrogen bond was observed between the hydroxyl group (donor) and the nitrile nitrogen atom (acceptor).
- A linear C-N⋯H acceptor geometry was confirmed, consistent with bonding theory.
- Each molecule acts as both a hydrogen bond donor and acceptor, leading to the formation of extended hydrogen-bonded chains along the [100] direction.
Conclusions:
- The crystal structure of (2-bromo-phenyl)-(hydroxy)acetonitrile is characterized by a well-defined intermolecular hydrogen bonding network.
- This hydrogen bonding dictates the formation of one-dimensional chains, influencing the overall supramolecular architecture.
- The study provides insights into the solid-state behavior of this functionalized acetonitrile derivative.