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CHEM 286L – Organic Chemistry Laboratory II Synthesis of Sulcatol

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CHEM 286L – Organic Chemistry Laboratory II Synthesis of Sulcatol Powered By Docstoc
					                                 D E PA RT M E N T O F C H E M I S T RY


                             CHEM 286L – Organic Chemistry Laboratory II

                                                 Synthesis of Sulcatol (Part 2)



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 Rf values that the
                ketone starting material.

 Chemical       The 6-methyl-5-hepten-2-one was reduced to the corresponding alcohol (sulcatol) previously and the

  reaction      crude product will be purified by distillation in the second part of the experiment.

                                               O                                   OH
                                                                 1. NaBH4

                                                                 2. H+, H2O


 Procedure      Distillation of Sulcatol: Pay close attention to the distillation Set-up shown in the lab. Try to
                reproduce it as accurately as possible.

                Using a pipette, transfer your sulcatol (Crude) into a 10 mL round bottom flask, add a stir bar, and
   Step 1
                attach it to your set-up. Start your water aspirator, and carefully “bubble off” the traces of ether
                present in the flask (Pay attention to the Instructor Demo). Once all the ether was removed, start your
                distillation by turning the heat up. Collect your distilled sulcatol in your Hickman’s head, and using a
                pipette, transfer it into a previously tarred clean 1-dram vial.
   Step 2
                Take an IR of your final compound.

                IMPORTANT: during the distillation make sure to carefully report in your lab notebook the
                distillation temperature along with the distillation pressure.

				
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