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Related Concept Videos

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

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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.
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Preparation of Alcohols via Substitution Reactions01:38

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Overview
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.

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Related Experiment Video

Updated: Jun 5, 2026

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
09:08

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Published on: April 2, 2018

Redetermination of 4-hydroxy-benzaldehyde.

Jerry P Jasinski, Ray J Butcher, B Narayana

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study precisely redetermined the crystal structure of C(7)H(6)O(2). Molecules form zigzag chains via hydroxyl and aldehyde group interactions, revealing detailed crystal packing.

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    Area of Science:

    • Crystallography
    • Solid-state chemistry

    Background:

    • The crystal structure of C(7)H(6)O(2) was initially reported by Iwasaki in 1977.
    • Previous structural data may lack the precision required for detailed analysis.

    Purpose of the Study:

    • To perform a high-precision redetermination of the crystal structure of C(7)H(6)O(2).
    • To elucidate the intermolecular interactions and crystal packing in C(7)H(6)O(2).

    Main Methods:

    • Single-crystal X-ray diffraction.
    • Structure refinement using modern crystallographic techniques.

    Main Results:

    • The crystal structure of C(7)H(6)O(2) was determined with enhanced precision.
    • Intermolecular O-H⋯O interactions between hydroxyl and aldehyde groups were identified.
    • These interactions stabilize the crystal packing, forming zigzag chains along the [110] plane.

    Conclusions:

    • The precise crystal structure of C(7)H(6)O(2) has been established.
    • The hydrogen bonding network dictates the molecular arrangement and crystal stability.
    • This work provides a more accurate structural model for C(7)H(6)O(2).