Hydroboration/Oxidation of Alkenes

Soobeen Park 4

Hydroboration/Oxidation of Alkenes

Introduction

The purpose of this lab was to transform an alkene (styrene) to an alcohol compound (2-phenyl ethanol) using hydroboration and oxidation reactions. This addition reaction is anti-Markovnikov, and yields a primary alcohol with the alcohol group attached to the least substituted carbon. The final product was analyzed using IR spectroscopy to test if the product was an alcohol.

Procedure

The procedure in the lab was followed as outlined in List, Adam. Chemistry 219A Organic Chemistry Laboratory. Fall 2014. The starting material was 1.7mL of styrene in 2mL of anhydrous THF solvent.

Results

Table 1: Theoretical, actual and percent yield of product (2-phenyl ethanol) by mass

Soobeen Park 1

Table 2: IR data, including relevant peaks, intensities and corresponding functional groups

Graph 1: Product IR spectrum Attached at the back of this report

Sample calculations:

-Theoretical yield:

-Percent yield:

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Conclusion

The percentage yield of the product was 25.2%,

which shows a significant loss of desired product during the experiment. The major source of the loss of product in this reaction was from the extraction/washing. Specifically, my organic and aqueous layers formed an emulsion when I tried to extract and wash, causing very much difficulty in accurately separating the two layers. Thus, there is a high chance that a lot of the desired product...