Synthesis Lab Report

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In this experiment, the competing enantioselective conversion (CEC) method was used to react an unknown secondary alcohol, which is either the R- or the S- enantiomer, with S-HBTM and R-HBTM separately. Thin-layer chromatography (TLC) was used to determine which reaction was faster. If the S-HBTM was faster, then the unknown secondary alcohol had the R configuration. If the R-HBTM was faster, then the unknown secondary alcohol had the S configuration. 1H NMR was used to determine the molecular structure of the unknown secondary alcohol.

There are couple factors that dictate the interaction of the unknown secondary alcohol and HBTM in this experiment. The first is due to steric strain; the phenyl group in HBTM forces the alcohol in the unknown to attack HBTM from the top face rather than the bottom face. Since both the unknown secondary alcohol and HBTM contain aromatic systems, the other factor that dictates their interaction is Pi-stacking, which brings the two compounds together. These two factors influence why the R enantiomer of the unknown secondary alcohol reacts faster with S-HBTM, and the S enantiomer of the unknown secondary alcohol reacts faster with R-HBTM. In the reaction between the R enantiomer of the unknown secondary alcohol and S-HBTM, for example, the alcohol in the …show more content…
TLC can be used to determine which reaction runs faster; if the ether spot from the S-HBTM reaction mixture is darker than the ether spot from the R-HBTM reaction mixture, then the conformation of the unknown secondary alcohol is R. And if the ether spot from the R-HBTM reaction mixture is darker than the ether spot from the S-HBTM reaction mixture, then the conformation of the unknown secondary alcohol is S. Using this information, along with an 1H NMR to determine structure, it was determine that unknown #1was

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