Reduction of 9-Fluorenone Post-lab Question #1: On the next page of this documen

Question

Reduction of 9-Fluorenone

Post-lab Question #1: On the next page of this document are the 1H and 13C NMR spectra of a saturated alcohol that has seven carbons. a) Determine the structure of the alcohol. (4 points)

b) How many isomers of the alcohol are there? (1 point)

c) Propose a synthesis of the alcohol starting from alcohols with 3 or fewer carbons. You may use any other reagents that you’d like. (4 points)

Post-lab Question #2: Explain why LiAlH4 is able to reduce esters and amides in addition to ketones and aldehydes while NaBH4 is only capable of reducing ketones and aldehydes. That is to say, why are esters and amides tougher to reduce than ketones and aldehydes, and why is a hydride from LiAlH4 more nucleophilic than a hydride from NaBH4? (4 points)

Explanation / Answer

LiAlH4 is beeter reducing agent than NaBH4. This is because,

(1) Compare the hydride structure in both. AlH4-and BH4-. Here aluminium being less electronegative it shift electron density towards hdrogen more than that of boron which more electronegative then aluminium.

(2) Compare the metals, Li+ is more electropositive than Na+, so, it can activate carbonyl more effectively than that of Na+ .

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