A. While both NaBH4 and LiAlH4 can both be used to reduce ketones and aldehydes, the...

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Chemistry

A. While both NaBH4 and LiAlH4 can both be used to reduceketones and aldehydes, the procedure that you followed in lab wouldnot result in the fluorenol product if NaBH4 were simply replacedwith LiAlH4.
i) Explain why.
ii) What change to the procedurewould have to be made to use LiAlH4 tosuccessfully reducefluorenone to fluorenol?
B. NaBH4 is not capable of reducing esters since estersare lessreactive than ketones. Explain structurally why this is thecase.
C. In a lab, NaBH4 is kept in a dessicator to avoid prolongedcontact with water in the atmosphere. This is done since waterwillreact with NaBH4. Write the balanced equation for the decompositionof NaBH4 by water.
D. It is found that a bottle of NaBH4 in a lab contains 70%NaBH4 by mass as a significant portion has reacted with atmosphericwater as described in question 3 above. What is the minimum that astudent should weigh out to fully reduce 3.18 g of fluorenone?

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3.6 Ratings (439 Votes)

BVery general mechanism of reduction of carbonyl compounds bymetal hydrides LiAlH4 NaBH4 is shown hereIts a simple nucleophilic addition of hydride ionH at carbonyl carbon Two factors aNucleophilicityand availability of Hydride ion and b Electrophilicity of carbonylC1KetonesAldehyde having carbonyl C substituted with eitheralkyl groupR or H atom An alkyl group have just Inductiveeffect on carbonyl carbon and thereby the stabilization of partialve charge charge on carbonyl C2In esters this alkyl substituent is replace by OR iealkoxygroup It has small I but larger R effect which See Answer

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