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Related Concept Videos

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.
IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...
IUPAC Nomenclature of Carboxylic Acids01:16

IUPAC Nomenclature of Carboxylic Acids

IUPAC names of carboxylic acids are systematically derived following a few rules discussed below.
For acyclic saturated monocarboxylic acids, the longest hydrocarbon chain containing the –COOH carbon is identified as the parent chain. Then, the last -e of the parent hydrocarbon name is replaced with a suffix -oic acid.
IUPAC Nomenclature of Ketones01:09

IUPAC Nomenclature of Ketones

Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing “e” in the name of the longest hydrocarbon chain with “one.” In acyclic ketones, the ketonic carbon is given the lowest locant value. For instance, as shown below, a simple five-carbon ketone is named pentan-2-one, instead of pentan-4-one. IUPAC rules also allow the placing of the locant value before the parent name to give an alternate name, 2-pentanone.
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.
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...

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Related Experiment Video

Updated: Jun 1, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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4-(3-Methoxy-phen-oxy)butyric acid.

Julia Heilmann-Brohl, Gérard Jaouen, Michael Bolte

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

    The crystal structure of a C(11)H(14)O(4) intermediate, crucial for synthesizing novel estrogen receptor modulators, reveals a planar arrangement and trans conformations. Molecules form dimers via hydrogen bonds, offering insights into drug design.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Medicinal Chemistry

    Background:

    • Estrogen receptor modulators are vital in treating hormone-dependent diseases.
    • Developing novel modulators requires understanding the structure of key synthetic intermediates.
    • The title compound, C(11)H(14)O(4), serves as a precursor in this synthesis.

    Purpose of the Study:

    • To elucidate the three-dimensional structure of the C(11)H(14)O(4) intermediate.
    • To analyze the molecular conformation and intermolecular interactions within the crystal lattice.
    • To provide structural data relevant to the design of new estrogen receptor modulators.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

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  • Analysis of bond lengths, bond angles, and torsion angles.
  • Identification and characterization of intermolecular interactions, including hydrogen bonds and C-H⋯O contacts.

    • Main Results:

    • All non-hydrogen atoms in the C(11)H(14)O(4) molecule lie on a common plane (r.m.s. deviation = 0.0472 Å).
    • The side chain exhibits trans conformations for all C-C bonds, with the hydroxyl group also in a trans orientation relative to the methylene chain.
    • Centrosymmetric dimers are formed through head-to-head arrangement stabilized by O-H⋯O hydrogen bonds; a weak C-H⋯O contact was also observed.

    Conclusions:

    • The determined crystal structure provides a detailed understanding of the C(11)H(14)O(4) intermediate's geometry.
    • The observed planar conformation and specific hydrogen bonding patterns are significant for its role in synthesizing estrogen receptor modulators.
    • This structural information can guide further optimization of drug candidates targeting the estrogen receptor.