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Related Concept Videos

Acid Halides to Carboxylic Acids: Hydrolysis01:01

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...
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
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...
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Leveling Effect and Non-Aqueous Acid-Base Solutions02:11

Leveling Effect and Non-Aqueous Acid-Base Solutions

This lesson defines the leveling effect in acidic and basic solutions and its role in aqueous and non-aqueous solutions. It is essential to understand the competing nature of various species in a chemical system.
The Leveling Effect of a Solvent
A generic acid (HA) reacts with the generic base (B-) to yield the corresponding conjugate base (A-) and conjugate acid (HB):

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Related Experiment Video

Updated: Jun 1, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Koetjapic acid chloro-form hemisolvate.

Z D Nassar, A F A Aisha, A M S Abdul Majid

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

    This study details the crystal structure of koetjapic acid, a complex organic molecule with a four-ring system. The research reveals its molecular arrangement and intermolecular interactions in a crystalline state.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Koetjapic acid is a natural product with a complex polycyclic structure.
    • Understanding its solid-state structure is crucial for elucidating its chemical properties and potential applications.

    Purpose of the Study:

    • To determine the precise three-dimensional structure of koetjapic acid in the crystalline state.
    • To analyze the molecular conformation, stereochemistry, and intermolecular interactions.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to collect diffraction data.
    • The crystal structure was solved and refined using crystallographic software.

    Main Results:

    • The asymmetric unit contains one disordered koetjapic acid molecule and a disordered chloroform solvent molecule.

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    Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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    Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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  • Koetjapic acid exhibits a fused four-ring system (A/B/C/D) with specific stereochemical configurations at the ring junctions.
  • Intermolecular O-H⋯O hydrogen bonds form dimers, which are further stacked along the c-axis.

    • Conclusions:

    • The crystal structure provides definitive insights into the molecular architecture of koetjapic acid.
    • The observed hydrogen bonding and packing arrangement influence the compound's solid-state behavior.