Stereoselective Reduction of Ketones with Sodium Borohydride- Microscale Reduction of Benzil

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Purpose: The reduction of carbonyl compounds is an important synthetic method to create alcohols. Aldehydes and ketones can be reduced by a variety of reagents to yield their respective alcohol products. Among the most useful reagents for accomplishing these reductions are the complex metal hydrides such as lithium aluminum hydride (LiAlH4 or LAH) and sodium borohydride (NaBH4). LAH and NaBH4 differ in their reactivities towards different classes of carbonyl compounds. LAH is highly reactive and will reduce acid chlorides, esters, carboxylic acids, amides, and nitriles as well as aldehydes and ketones. NaBH4 is less reactive and therefore more selective than LAH: it reduces aldehydes and ketones, but not carboxylic acids and amides, and only slowly reduces esters. NaBH4 is much safer to handle than is LAH, making it a good choice whenever the functional group to be reduced is an aldehyde or ketone. The purpose of the below methodology isto synthesize meso-hydrobenzoin from benzyl using the reducing agent sodium borohydride. Reaction and Mechanism: Formation of meso-hydrobenzoin | | Benzil | + | Sodium Borohydride | → | Hydrobenzoin | | C14H10O2 | | NaBH4 | | C14H14O2 | | | | | | | Molecular Wight | 210.23 g/mol | | 37.83 g/mol | | 214.26 g/mol | Observed Mass/Volume | 400 mg | | 150 mg | | 354.4 mg | Observed Moles | 1.902 mmol | | 3.96 mmol | | 1.65 mmol | Theoretical Yield | | | | | 407.52 mg | Percent Yield | | | | | 88.5 % | Theoretical Melting Point | 94-96 °C | | | | 137 °C | Observed Melting Point | | | | | 136.4-137.3 °C | Calculations: Observed Moles ofBenzil-0.2 g of Benzil x 1 mol210.23gmol=0.000951 mol→0.951 mmol x 2 reaction doubled=1.902 mmol Observed Moles ofSodium Borohydride-0.075 g of Sodium Borohydride x 1 mol37.83gmol=0.00198 mol→1.98 mmol x 2 reaction doubled=3.96 TY-0.000951 mol x 1

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