Lab 8 Borohydride Reduction - Experiment #8 Reaction of...

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Experiment #8 Reaction of Sodium Borohydride with Different Carbonyl Compounds 11/12/09
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Purpose The purpose of this experiment was to identify a given unknown from a selection of Benzaldehyde, Benzophenone, Ehtyl Benzoate, or Benzoic Anhydride. The carbonyl compound of choice was reduced with Sodium Borohydride, and quenched with water. This reduction breaks the double bond between the carbon and oxygen atoms and adds a hydrogen to both the carbon and the oxygen (the second hydrogen being borrowed from water). The products and original starting materials were analyzed using infrared spectrometry and melting point determination, as well as qualitative observations. Reactions See attached mechanisms sheet Results (Also see IRs of standards and products) Mass at Start Observations at Start Mass of Product Yield Observations about Products Unknown 1 600mg Liquid with cherry scent 391mg 65.08% Clear liquid Unknown 2 600mg White solid 500mg 83.3% Rose-like odor, white color solid (MP= 48.1-49.7 C) Unknown 3 Me 600mg Liquid with good smell 420mg 70% Clear liquid with a similar good smell Unknown 4 600mg White solid 426mg 71% White solid (MP=43 C) Calculations
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% Yeild = Mass of final product/ Mass of starting compound e.g. 420mg/600mg = 70% Discussion and Conclusion As shown in the reaction mechanisms, the borohydride attacks the carbonyl carbon, making the carbon chiral and the oxygen only single bonded. The negative oxygen then attacks a hydrogen connected to water, creating a hydroxyl group that can be
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Lab 8 Borohydride Reduction - Experiment #8 Reaction of...

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