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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...

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...

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

π Molecular Orbitals of the Allyl Cation and Anion

π Molecular Orbitals of the Allyl Cation and Anion

An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with an...

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.

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

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Related Experiment Video

Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

2-Cyano-anilinium perchlorate.

Li-Jing Cui¹, Xin-Yuan Chen

¹College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

The crystal structure of a nitrogen-containing compound revealed an almost planar cation. This cation, along with perchlorate anions, formed a two-dimensional network through hydrogen bonding in the solid state.

Area of Science:

Crystal chemistry
Solid-state chemistry
Supramolecular chemistry

Background:

Understanding the packing and interactions of organic cations with inorganic anions is crucial in crystal engineering.
The study of hydrogen bonding provides insights into the self-assembly of crystalline materials.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(7)H(7)N(2) (+)·ClO(4) (-).
To investigate the intermolecular interactions, specifically hydrogen bonding, governing the crystal packing.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
Analysis of bond lengths, bond angles, and intermolecular distances to identify hydrogen bonding patterns.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Main Results:

The crystal structure consists of discrete cations, C(7)H(7)N(2) (+), and perchlorate anions, ClO(4) (-).
The cation exhibits a nearly planar geometry with a root-mean-square deviation of 0.042 Å.
A two-dimensional network structure was observed, formed by N-H⋯O hydrogen bonds linking cations and anions parallel to the (100) plane.

Conclusions:

The title compound forms a robust two-dimensional supramolecular network through directed N-H⋯O hydrogen bonding.
The planar nature of the cation and the specific hydrogen bonding interactions dictate the observed network architecture in the solid state.