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10.5: Polar and Non-Polar E-H Bonds

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    Hydride reducing agents

    LiH and Al2Cl6 gives lithium aluminium hydride (lithal LiAlH4), NaH reacts with B(OCH3)3 to give sodium borohydride (NaBH4). These find wide scope and utility in organic chemistry as reducing agents.

    LiAlH4 is commonly used for the reduction of esters and carboxylic acids to primary alcohols; previously this was a difficult conversion that used sodium metal in boiling ethanol (the Bouveault-Blanc reduction). The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.

    NaBH4 is used in large amounts for the production of sodium dithionite from sulfur dioxide: Sodium dithionite is used as a bleaching agent for wood pulp and in the dyeing industry. NaBH4 consists of the tetrahedral BH4- anion in the crystalline form and is found to exist as three polymorphs: α, β and γ. The stable phase at room temperature and pressure is α-NaBH4, which is cubic and adopts an NaCl-type structure. Millions of kilograms are produced annually, far exceeding the production levels of any other hydride reducing agent.

    NaBH4 will reduce many organic carbonyls, depending on the precise conditions. Most typically, it is used in the laboratory for converting ketones and aldehydes to alcohols. For example, reduction of acetone (propanone) to give propan-2-ol.

    reaction of acetone to propan-2-ol

    10.5: Polar and Non-Polar E-H Bonds is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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