The goal of experiment four was to use sodium dichromate to oxidize borneol to camphor. The camphor was purified using sublimation, then reduced to isomeric alcohol isoborneol with sodium borohydride. 1H NMR was used to determine the ratio of borneol to isoborneol in the final product.
The experiment was carried out by using sodium dichromate to oxidize a borneol solution. Once the reaction was complete the mixture was separated using extraction techniques, dried, and ether was removed via the rotovap. When solid was formed the product was purified using sublimation. The final product (camphor) was tested for its melting point and an IR spectrum was obtained. To reduce the camphor to isoborneol sodium borohydride was used. Once this …show more content…
The true value melting point for camphor is 174°C, however the depression in the melting point indicates an impurity. The impurity would most likely be borneol because both camphor and borneol sublime and there wasn’t full control over the heat so when purified both products sublimed. As found on the website chemwiki, with even a small impurity of borneol the melting point of camphor will drastically decrease. The melting point of the recovered product in part two which is isoborneol was 170°C. The true value melting point for isoborneol is 212°C. The depression in the melting point for isoborneol would also be an impurity of borneol, as indicated in the IR spectrum of isoborneol still showing a carbonyl group. Based on the results of the melting point, even though there was some impurity, it gives evidence that the transformation may have not gone to completion in both …show more content…
The percent yield of isoborneol (part two) was determined to be 36.7% with the limiting reagent being camphor. If this reaction was repeated, more care would have been taken when subliming the product by controlling the temperature to make sure only camphor and isoborneol got sublimed. However, based on the IR spectra’s obtained camphor and isoborneol, the reaction did successfully oxidize borneol to camphor showing the formation of the key carbonyl group, and the reaction to reduce camphor to isoborneol did somewhat go to completion with the key hydroxyl group but it did show a carbonyl group present, which is not present in the true isoborneol IR spectrum. The 1H NMR also showed good experimental evidence of isoborneol being preferred (major product) over
The experiment was carried out by using sodium dichromate to oxidize a borneol solution. Once the reaction was complete the mixture was separated using extraction techniques, dried, and ether was removed via the rotovap. When solid was formed the product was purified using sublimation. The final product (camphor) was tested for its melting point and an IR spectrum was obtained. To reduce the camphor to isoborneol sodium borohydride was used. Once this …show more content…
The true value melting point for camphor is 174°C, however the depression in the melting point indicates an impurity. The impurity would most likely be borneol because both camphor and borneol sublime and there wasn’t full control over the heat so when purified both products sublimed. As found on the website chemwiki, with even a small impurity of borneol the melting point of camphor will drastically decrease. The melting point of the recovered product in part two which is isoborneol was 170°C. The true value melting point for isoborneol is 212°C. The depression in the melting point for isoborneol would also be an impurity of borneol, as indicated in the IR spectrum of isoborneol still showing a carbonyl group. Based on the results of the melting point, even though there was some impurity, it gives evidence that the transformation may have not gone to completion in both …show more content…
The percent yield of isoborneol (part two) was determined to be 36.7% with the limiting reagent being camphor. If this reaction was repeated, more care would have been taken when subliming the product by controlling the temperature to make sure only camphor and isoborneol got sublimed. However, based on the IR spectra’s obtained camphor and isoborneol, the reaction did successfully oxidize borneol to camphor showing the formation of the key carbonyl group, and the reaction to reduce camphor to isoborneol did somewhat go to completion with the key hydroxyl group but it did show a carbonyl group present, which is not present in the true isoborneol IR spectrum. The 1H NMR also showed good experimental evidence of isoborneol being preferred (major product) over