Sulcatol-Part1 - D E PA RT M E N T O F C H E M I S T RY...

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DEPARTMENT OF CHEMISTRY CHEM 286L – Organic Chemistry Laboratory II Synthesis of Sulcatol ( Part 1 ) Introduction Sodium borohydride reduction is a convenient way to synthesize alcohols from aldehydes or ketones. If the ketone starting material is unsymmetrically substituted, the resulting alcohol will be chiral. However, as the carbonyl group is planar, the reducing agent can transfer the hydride ion as easily from the top of the molecule as from the bottom and a racemic mixture is produced. TLC can easily check the progress of the reduction, as the alcohol product generally has smaller R f values that the ketone starting material. Chemical reaction The 6-methyl-5-hepten-2-one will be reduced to the corresponding alcohol (sulcatol) and the product will be purified by distillation in the second part of the experiment. O 1. NaBH 4 2. H + , H 2 O OH Textbook reference Chapter 17.6 Chapter 19.1 Sodium borohydride reductions involve nucleophilic addition of hydride ions (H - ) to the carbonyl
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This note was uploaded on 10/16/2010 for the course CHEM 286L taught by Professor Kreis during the Fall '10 term at Simon Fraser.

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Sulcatol-Part1 - D E PA RT M E N T O F C H E M I S T RY...

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