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Related Concept Videos

Acid Strength and Molecular Structure03:05

Acid Strength and Molecular Structure

Binary Acids and Bases
In the absence of any leveling effect, the acid strength of binary compounds of hydrogen with nonmetals (A) increases as the H-A bond strength decreases down a group in the periodic table. For group 17, the order of increasing acidity is HF < HCl < HBr < HI. Likewise, for group 16, the order of increasing acid strength is H2O < H2S < H2Se < H2Te. Across a row in the periodic table, the acid strength of binary hydrogen compounds increases with increasing...
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...
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Acidity of Carboxylic Acids01:21

Acidity of Carboxylic Acids

Carboxylic acids are the strongest organic acids. However, their acidic strength is much less than mineral acids like HCl. Carboxylic acids ionize in water and readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion.
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes


The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.

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Related Experiment Video

Updated: May 24, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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(3R,4S,5S,8S,10R,13R)-3-Hy-droxy-kaura-9(11),16-dien-18-oic acid.

Karren D Beattie, Mohan M Bhadbhade, Donald C Craig

    Acta Crystallographica. Section E, Structure Reports Online
    |February 21, 2012
    PubMed
    Summary

    Researchers isolated a novel enanti-pure diterpene from Centipeda cunninghamii. This compound features a unique carbon skeleton and specific ring conformations, with its absolute configuration determined by optical rotation.

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    Area of Science:

    • Phytochemistry
    • Organic Chemistry
    • Structural Chemistry

    Background:

    • Centipeda cunninghamii (Asteraceae) is a plant species known for its potential medicinal properties.
    • Investigations into the chemical constituents of medicinal plants are crucial for discovering novel bioactive compounds.

    Purpose of the Study:

    • To isolate and characterize a novel compound from Centipeda cunninghamii.
    • To determine the chemical structure, including stereochemistry, of the isolated compound.
    • To understand the intermolecular interactions in the crystal lattice.

    Main Methods:

    • Isolation and purification of the title compound (C20H28O3) from Centipeda cunninghamii.
    • Spectroscopic analysis for structural elucidation.
    • X-ray crystallography to determine the conformation and hydrogen bonding.
    • Optical rotation measurements for assigning absolute configuration.

    Main Results:

    • An enanti-pure diterpene with a unique carbon skeleton was isolated.
    • The compound possesses three six-membered rings and one five-membered ring with specific conformations (chair, twist-boat, half-chair, envelope).
    • Intra- and inter-molecular hydrogen bonds were observed, forming chains in the crystal lattice.

    Conclusions:

    • The study successfully identified and characterized a novel diterpene from Centipeda cunninghamii.
    • The detailed structural analysis provides insights into the compound's molecular architecture and solid-state behavior.
    • The absolute configuration was established, which is vital for understanding its potential pharmacological activity.