Kinetic Production of Isoborneol through the Oxidation-reduction Sequences of Borneol

Kinetic Production of Isoborneol through the Oxidation-reduction Sequences of Borneol

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Through an oxidation-reduction reaction sequence, Borneol is converted to isoborneol. First, borneol is oxidized through a reaction with sodium hypochlorite at 400C to form camphor. When the camphor is then reduced by sodium borohydride, isoborneol is formed. The percent yeild of isoborneol collected was 56.4%, and the melting point range was found to be between 174.2-179.90C. Through analysis of the product through 1H NMR spectroscopy the percent purity is found to be 77.2% pure isoborneol.

Introduction

Oxidation-reduction reactions can be used to stereochemically control and produce many different organic molecules. The oxidation step in this process increases the number of carbon oxygen bonds by losing a hydrogen and breaking that bond. Through the reduction step, carbon-oxygen bond is broken and the hydrogen is returned.

In the oxidation of borneol to camphor, a hydrogen is removed from the carbon attached to the hydroxy group. In order for the all the atoms to have octets, the charged carbon forms double bonds with the oxygen atoms. The product produced is camphor.

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The camphor then went through reduction with sodium borohydride to make isoborneol. This reaction was able to be stereochemically controlled by limiting the amount of heat we provided. The conversion of camphor to isoborneol has a lower

activation energy than what is required to turn camphor into borneol. Though borneol is the more stable product, the energy requirements to form isoborneol are lower because the borohydride is adding to the less sterically hindered point on the carbonyl carbon. The product made is then mostly (85%) isoborneol. More borneol would be expected if more energy was available during the reaction.
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...his purity calculation doesn't account for the singnal at 2.10ppm corresponding to the acetone in the product. Niether does it account for the signal belonging to CHCl3 at 7.12ppm. This information along with the 33% borneol can be used to account for the low melting point range.

The isoborneol produced through this redox reaction was the kinetic product. This kinetic product was less stable, yet it was produced because of the low amount of energy supplied for the reaction. In the formation of isoborneol the hydride ion attacks the carbonyl carbon of camphor on the least hindered site. With more energy the molecules have more effective collisions on the opposite side. With the energy supplied in this reaction, there would be too much steric effect inhibiting the hydride ion from attacking the carbonyl carbon to make the more stable thermodynamic product borneol.

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