Lecture 7 with ink

Lecture 7 with ink - Nature of Selectivity: ore of the...

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Winter 2009 Lecture 7
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Experiment 7
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O H OH t -Bu H t -Bu OH H t -Bu H 80:20 + trans cis MeOH NaBH 4 , NaOMe odium orohydride aBH 4- tert -butylcyclohexanol 4 -tert -butylcyclohexanone Sodium Borohydride NaBH 4 BH 4 - has the potential to add 4 hydrogens. The mechanism is on an upcoming slide Terms for rxn’s that gives chiral products: Stereoselective- more of one than another (this action is stereoselective reaction is stereoselective Stereospecific- only one stereoisomer formed
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The products are diastereomers If there is one chiral center in a compound, and a new one is made, then the product(s) that result are diastereomers. Diastereomers have different physical properties, so you can see them travel differently on the TLC
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Unformatted text preview: Nature of Selectivity: ore of the trans product is formed because it puts ◦ More of the trans product is formed because it puts the alcohol on the equatorial axis. This minimizes any 1,3-diaxial repulsion. Mechanism: NOTE: You will use TLC to tell you when the experiment is completed. If you take a TLC and it still shows there is starting material, dd another equivalent of reagents Repeat add another equivalent of reagents. Repeat this process until no starting material remains by TLC. This may require you to take a few TLC’s and/or add more equivalents of the sodium borohyride reagent....
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This note was uploaded on 04/09/2010 for the course CHEM 6a taught by Professor Pettus during the Winter '07 term at UCSB.

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Lecture 7 with ink - Nature of Selectivity: ore of the...

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