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Related Concept Videos

Preparation of Acid Anhydrides01:07

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...
Reactions of Acid Anhydrides01:19

Reactions of Acid Anhydrides

The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.

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Related Experiment Video

Updated: Jun 1, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

α-Costic anhydride.

Mohamed Tebbaa, Mohamed Akssira, Ahmed Elhakmaoui

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    A new isocostic anhydride was synthesized from Inula Viscosa. Its molecular structure features fused rings bridged by an anhydride group, forming a linear shape with specific ring conformations.

    Area of Science:

    • Natural Product Chemistry
    • Organic Chemistry
    • Crystallography

    Background:

    • Inula Viscosa (Dittrichia Viscosa) is a plant source of bioactive compounds.
    • Isocostic anhydrides represent a class of organic molecules with potential chemical interest.

    Purpose of the Study:

    • To synthesize and characterize a novel isocostic anhydride from Inula Viscosa.
    • To elucidate the molecular structure and crystal packing of the synthesized compound.

    Main Methods:

    • Chemical synthesis of the title compound from aerial parts of Inula Viscosa.
    • X-ray crystallography to determine the molecular and crystal structure.
    • Analysis of molecular conformation and intermolecular interactions.

    Main Results:

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    • Successful synthesis of a new isocostic anhydride: 2-(4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octa-hydro-naphthalen-2-yl)acrylic acid anhydride.
    • The molecule exhibits a linear conformation with two terminal fused rings bridged by an anhydride group.
    • Crystal structure reveals specific ring conformations (half-chair and chair) and 2D array formation via C-H⋯O interactions.

    Conclusions:

    • The study reports the discovery and structural characterization of a new isocostic anhydride.
    • The findings provide insights into the stereochemistry and solid-state behavior of this class of compounds.
    • This research contributes to the understanding of natural product derivatives from Inula Viscosa.