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Related Concept Videos

Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt condensation is...
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...

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Related Experiment Video

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

4-Hex-yloxy-3-methoxy-benzaldehyde.

Asghar Abbas, M Khawar Rauf, Michael Bolte

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details a synthetic vanillin analogue, C(14)H(20)O(3), featuring a long aliphatic side chain. Structural analysis reveals two independent molecules in the asymmetric unit, both exhibiting near-planar conformations.

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    Area of Science:

    • Food Chemistry
    • Crystallography
    • Organic Synthesis

    Background:

    • Vanillin is a widely used food additive and flavoring agent.
    • Synthetic analogues are explored to understand structure-activity relationships.
    • The compound C(14)H(20)O(3) is a novel synthetic analogue of vanillin.

    Purpose of the Study:

    • To synthesize and characterize a novel vanillin analogue.
    • To elucidate the molecular conformation and crystal structure of the synthetic compound.
    • To investigate the structural impact of a long aliphatic side chain on vanillin analogues.

    Main Methods:

    • Chemical synthesis of the title compound C(14)H(20)O(3).
    • Single-crystal X-ray diffraction analysis to determine molecular and crystal structure.
    • Conformational analysis based on crystallographic data.

    Main Results:

    • The synthetic compound C(14)H(20)O(3) was successfully prepared.
    • Two independent molecules were identified in the asymmetric unit of the crystal.
    • Both molecules displayed essentially planar conformations, with low root-mean-square deviations for non-hydrogen atoms.

    Conclusions:

    • The synthetic vanillin analogue C(14)H(20)O(3) possesses a near-planar molecular structure.
    • The long aliphatic side chain does not induce significant deviations from planarity in this analogue.
    • Structural insights were gained into vanillin analogues with extended side chains.