a. For the reduction reaction with NaBH4, calculate the theoretical yield and percent yield of the crude product after liquid-liquid extraction. Assume the ketone is the limiting reactant, and your alcohol product has a molar mass that is 2 amu larger than the ketone starting material. Show all calculations. Mass of empty 50 mL round-bottomed flask: 39.8791 g Mass of 50 mL round-bottomed flask with crude reduction product (Step 16): 39.9585 g Appearance of crude reaction product: colorless oil

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Though NaBH4 and LiAlH4 are similar, NaBH4 is less reactive. Esters, amides, acids, and nitriles are largely unaffected; its power is limited to reducing aldehydes, ketones, and acid chlorides to alcohols.

Because the hydride ion can attack the planar carbonyl group on either face, the reduction of unsymmetrical ketones with LiAlH4 or NaBH4 results in the production of two stereoisomers: A racemic mixture of enantiomers results from the absence of any additional chiral centers. The intermediates produced by the reaction of sodium borohydride with water are also mild reducing agents known as hydroxyborohydride. The most popular reaction solvents for reduction or organic substrates are ethanol and propane-2-ol, though methanol is also employed. Because a similar reaction with alcohol is relatively slow, it is also known as an alcohol reduction reaction.

Theoretical yield = (Actual yield/percentage yield) x 100

Percent Yield = Mass of Actual Yield / Mass of Theoretical Yield x 100 percent

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