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Acid Halides to Carboxylic Acids: Hydrolysis

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...

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.

Preparation of Acid Anhydrides

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...

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...

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.

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Aldehydes 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...

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Updated: Jun 1, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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2-(2-Chloro-phen-oxy)acetohydrazide.

Hoong-Kun Fun, Ching Kheng Quah, Arun M Isloor

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

The crystal structure of C(8)H(9)ClN(2)O(2) reveals a planar acetohydrazide group. Molecules form infinite sheets via hydrogen bonding, highlighting intermolecular interactions in crystal engineering.

Area of Science:

Crystallography
Chemical Physics

Background:

Understanding molecular interactions is crucial for materials science.
Crystal structure analysis provides insights into intermolecular forces.

Purpose of the Study:

To determine the crystal structure of the title compound C(8)H(9)ClN(2)O(2).
To investigate the hydrogen bonding network and molecular arrangement in the crystal.

Main Methods:

Single-crystal X-ray diffraction was used to analyze the crystal structure.
Analysis of hydrogen bond donors and acceptors to elucidate intermolecular interactions.

Main Results:

The acetohydrazide group within C(8)H(9)ClN(2)O(2) was found to be approximately planar (maximum deviation of 0.031(2) Å).

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Molecules are interconnected through a network of N-H⋯N, N-H⋯O, and C-H⋯O hydrogen bonds.

The acetohydrazide oxygen atom acts as an acceptor for two C-H⋯O and one N-H⋯O hydrogen bond.

These interactions lead to the formation of infinite sheets parallel to the (100) crystallographic plane.

Conclusions:

The study elucidates the detailed crystal packing of C(8)H(9)ClN(2)O(2).
The identified hydrogen bonding patterns dictate the formation of sheet-like structures, relevant for crystal engineering and supramolecular chemistry.