Sodium borohydride reduction of 2-Methylcyclohexanone

Kella Ortega, Miguel Fernandez, Andrei Maghirang

Experiment performed July 15, 2013; final report submitted August 25, 2013

A reduction reaction was done on a 2-methylcyclohexanone to form a 2-
methylcyclohexanol. The product made was a white liquid solution, despite the fact that 2-
methylcyclohexanol is supposed to be colorless. This was accountable to the error committed by
the group in regulating the temperature of one of the reactants. The group was unable to analyze
the product through the IR spectrum or the MS. This is due to the limited amount of product
produced and errors committed by the group with regards to handling the product. In addition,
the properties of the product (melting point, density, etc.) had not been tested.

Reduction of sodium borohydride was discovered in 1943 by H. I. Schlesinger and H. C.
Brown. Brown devoted his entire scientific career to this reagent, making it and other hydrides
the most useful and versatile of reducing reagents. The principal application of sodium
borohydride is the production of sodium dithionite from sulfur dioxide; sodium dithionite is used
as a bleaching agent for wood pulp and in the dyeing industry. Sodium borohydride reduces
aldehydes and ketones to give the related alcohols. This reaction is used in the production of
various antibiotics including chloramphenicol, dihydrostreptomycin, and thiophenicol. Various
steroids and vitamin A are prepared using sodium borohydride in at least one step.
Reduction is a reaction that involves an increase in number of electrons in a molecule.
For example, metabolism, a chemical process that is responsible for the different processes that
keep organisms alive, is driven by Redox reactions. This reaction is usually accompanied by
another reaction called oxidation reaction. An oxidation reaction is characterized by a decrease in
number of electrons by another molecule. In these two reactions, the organic compound and the
reagent may be the reducing agent or the oxidizing agent, depending on the whole reaction. The
reducing agent is the compound that experiences oxidation while it reduces or it takes the proton
from the other compound. On the other hand, the oxidizing agent is the compound that
experiences reduction, while it oxidizes or gives the proton the other compound. In this
experiment, reduction is seen when the 2-methylcyclohexanone was reduced by the sodium
borohydride when it was added to the reaction6.

3 g/cm3 and it would be easily soluble in cold water1.9240 g/cm and it can be soluble in methanol.172 g/mol. formation of 2-Methylcyclohexanol Figure 1: Mechanism. Methanol is a liquid that has a molecular weight of 32.1 degC. The reactants used were sodium borohydride and methanol.8 degC. diethyl ether.11 g/cm . formation of 2-Methylcyclohexanol The starting material.5degC. Its density is 1. Its boiling point is 165. It is insoluble in cold water. is liquid with a molecular weight of 3 112. Its 3 boiling point is 64.83 g/mol. It is soluble in both cold and hot water3. Figure 1: Reaction. it decomposes. while its melting point is 97. At melting point. Its density is 1. It has a density of . Sodium borohydride is solid with a molecular weight of 37. and acetone.04 g/mol. 2 . 2-methylcyclohexanone.

It was then boiled under the hood. Among other things. the experimenters were not able to witness the expected change of becoming murky in the appearance of the solution. leaving what was the expected product on the reaction tube5. However. the expected product of this experiment is 2-methylcyclohexanol. borate ester. 3 . The sample was too small to run be run on both IR and MS. This is usually used to form a mixture of cyclic alkenes which has become a standard experiment in the organic chemistry and upper-level laboratory curricula at several colleges and universities. The solution was then transferred to a dry reaction tube which had a couple of boiling chips in it.25 mL of M sodium hydroxide solution. After letting the solution settle. The upper layer was placed in a reaction tube. The resulting reaction. the expected clarity of the solution was not seen even after the reaction ended.5 mL dichloromethane. After adding the sodium hydroxide. The reaction tube was then cooled in an ice bath. the by-products Na. it was placed in a separatory funnel and 1 mL of water was added. since the organic product is theorized to have less density.25 mL of methanol and 300 mg of 2-methylcyclohexanone was added in a reaction tube. If done properly. It was boiled for only a short time so that most of the dichloromethane and methanol would evaporate. in the end. the group decided to run it through MS. The extracts where then dried with use of anhydrous sodium sulfate. it was cooled for 10 minutes5. While inside the ice bath. the group was not able to get the results of the run since the product was taken out of the machine and replaced with other solutions before the group was able to see the results of the run5. BH 3 and OCH3 were also expected to be made6. However. After adding sodium borohydride. The reaction separated into layers. Then it was extracted two times with the use of 0. 2-methylcyclohexanol. So. since the solution was already murky even before the sodium hydroxide was added. because one member of the group accidentally placed it in the ice bath. Methodology A combination of 1. 50 mg of sodium borohydride was added. this compound illustrates the utility of Zaitsev's rule. was then decomposed by adding 1. This may be because the added sodium borohydride was colder than room temperature. Other than the aimed product.

50 mg of sodium borohydride was added. Then. which in turn would make the oxygen atom negatively charged. It is slightly soluble and its density is supposedly 0. In the experiment. In the mechanism of the reaction. neutralizing the charge in the oxygen atom and making 2-methycyclohexanol. Other than its theoretical appearance.930 cm3 . while its boiling point is supposed to g be from 163 . However. the solution was set aside to cool for 10 minutes. Sodium borohydride was added into the solution while the solution was in an ice bath in order to keep tominimize the temperature.19 mol . After this procedure. an error was still committed in this procedure since the sodium borohydride added was not in room temperature. 4 . while it was still in the ice bath. Also. 2 Results and Discussion The experiment’s main objective is to experimentally show the process of reduction of 2- methylcyclohexanone. the carbonyl carbon in the 2- methylcyclohexanone would reduce the sodium borohydride by taking one of the hydrogen atoms. a side reaction between sodium borohydride and methanol would occur. which made it possible for the sodium borohydride to attack either from the front or the back of the 2-methycyclohexanone. but instead was accidentally cooled by an ice bath before it was added to the solution.25 mL of methanol and 300 mg of 2-methylcyclohexanone were combined in a reaction tube. it is supposed to be clear or colorless. The resulting reaction was borate ester.166 deg C. 1. If the temperature was not properly controlled. This may still be due to the error committed earlier in the experiment. After the reaction. Two products were formed because the reagent had a stereocenter. the experimenters were able to note that the color of the product was white. Its g C7 H 14 O molecular formula is . According to theory. The negatively charged oxygen would then take a proton from ethyl alcohol. the reaction tube was cooled in an ice bath. its odor is said to be associated with menthol. This solution was murky. However. the group was unable to retrieve data regarding most of the physical properties of the product during the experiment because it was advised to not do so with the limited given to complete the experiment. The new bond in the carbonyl carbon would cause the double bond between the carbon and oxygen atom to break. however. and its molecular weight is 114.

The expected product was the top-most layer.25 mL of M sodium hydroxide solution. If the experiment was a success. The experimenters should have thoroughly been present as the product was undergoing MS. the solution was dried through the use of anhydrous sodium sulfate. This caused the reaction to separate into 2 layers. There were many errors committed in this experiment. So. This was then decomposed through the addition of 1. the product may not truly be what was expected. it would have a peak alike the one found in 1452. respectively. which represents the presence of benzene. Then. After drying the solution. especially since there were significant errors committed by the group as they were conducting the experiment. it would be advisable to check the procedures before such things are done. Also. the IR spectrum of the product would be similar to that of the IR spectrum of a 2-methylcyclohexanol (Appendix 1). It is theorized that the murkiness of the solution is caused by the error committed with regards to the temperature of sodium borohydride. In addition.73 and 2938.73.5 mL of dichloromethane.07 represent the presence of alcohol and alkyl groups.despite the fact that it should not be. This layer underwent extraction two times with 0. The other error committed was leaving our product to run on its own in the MS. it was briefly boiled under the hood to evaporate most of the substances that were not the expected product. the other members of the group should be more vigilant in checking what the other members do in order to prevent such other mishaps from occurring. it was transferred to a separatory funnel and 1 mL of water was added. It is recommended that the researchers follow the procedures of the experiment thoroughly because anything that was changed or done unnecessarily may have unwanted outcomes like a lessened 5 . the group finds it hard to scope the success of the experiment conducted. drying it was supposed to take out the water in the solution. This is because organic substances usually have less density. Dichloromethane was used since it has a higher density than water. Next time. it was transferred to a reaction tube which contained boiling chips. The peaks in 3351. It needed to be dried because there was still water inside the solution. The expected change in the solution's texture was not seen because the solution was already murky to begin with. After which. Then. Conclusion and Recommendations As the product had not been tested. The first being that one member of the group accidentally decreased the temperature of sodium borohydride. 2 – Methylcyclohexanol5.

(n. References 1 Material Safety Data Sheet. 2013. Science Lab. Knowing the difference between the experimental and the theoretical yield would help the group know if they efficiently conducted the experiment or not. 2013.sciencelab. Fisher Scientific.d. Science the group should always take note of the yield they obtained after every experiment so they may have a point of comparison with the theoretical value. Retrieved August 24. R. from http://www. & Zumdahl. 6 Zumdahl. 2013.d.php?msdsId=9924969 2 Material Safety Data Sheet. Boston: Houghton Mifflin S. Macroscale and microscale organic experiments (5th ed. Science Lab. 2013.). from http://fscimage. (2012).. S. Retrieved August 24. 6 . from http://www. Retrieved August 24. (n.). K.. To add to that. K. (n.sciencelab.d.php?msdsId=9927227 4 Material Safety Data Sheet. Masters.). (n.yield or obtaining different reactions.htm 5 Williamson.). Minard..fishersci.). Retrieved August 24.php?msdsId=9923625 3 Material Safety Data Sheet. (2007). Belmont: Cengage Learning. from http://www.d.Chemistry: An Atoms First Approach .

Appendices Appendix 1 – IR spectrum of 2-Methylcyclohexanol 7 .