OBJECTIVE

1. To synthesis of cyclohexanol from cyclohexanone by using reduction reaction with sodium borohydride.

INTRODUCTION In organic chemistry, a ketone is a compound with the structure RC(=O)R', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group (C=O) bonded to two other carbon atoms. Acetone is the simplest example of a ketone, and in fact the word ketone derives its name from Aketon, the German word for acetone. The ketone carbon is often described as "sp2 hybridized," terminology that describes both their electronic and molecular structure. Ketones are trigonal planar about the ketonic carbon, with C-C-O and CC-C bond angles of approximately 120°. The carbonyl group is polar as a consequence of the fact that the electronegativity of the oxygen center is greater than that for carbonyl carbon. Thus, ketones are nucleophilic at oxygen and electrophilic at carbon. Because the carbonyl group interacts with water by hydrogen bonding, ketones are typically more soluble in water than the related methylene compounds. Ketones are a hydrogen-bond acceptors. Ketones are not usually hydrogen-bond donors and cannot hydrogen-bond to itself. Because of their inability to serve both as hydrogen-bond donors and acceptors, ketones tend not to "self-associate" and are more volatile than alcohols and carboxylic acids of comparable molecular weights. These factors relate to pervasiveness of ketones in perfumery and as solvents.

Sodium borohydride, also known as sodium tetrahydridoborate, is an inorganic compoundwith the formula NaBH4. This white solid, usually encountered as a powder, is a versatilereducing agent that finds wide application in chemistry, both in the laboratory and on a technical scale. Large amounts are used for bleaching wood pulp. The compound is insoluble in ether, andsoluble in glyme solvents, methanol and water, but reacts with the latter two in the absence of base. The compound was discovered in the 1940s by H. I. Schlesinger, who led a team that developed metal borohydrides for wartime applications. Their work was classified and published only in 1953.

Again. a complex similar to the previous one is formed. NaOH . water is added and the mixture is boiled to release the alcohol from the complex. It can be used in solution in alcohols or even solution in water provided the solution is alkaline. At the end of this time. CH3OH. Solid sodium tetrahydridoborate is added to a solution of the aldehyde or ketone in an alcohol such as methanol.Sodium tetrahydridoborate is a more gentle (and therefore safer) reagent than lithium tetrahydridoaluminate. Depending on which recipe you read. ethanol or propan-2-ol. NaB H4 H2O. This almost certainly varies depending on the nature of the aldehyde or ketone. In this experiment cyclohexanone was reduce to cyclohexanol by sodium borohydride (NaBH4). it is either heated under reflux or left for some time around room temperature. In the second stage of the reaction. the alcohol formed can be recovered from the mixture by fractional distillation.

Mechanism for the above reaction: .

16.CH2 Cl2 .5 mL of cyclohexanone was otained and placed in a small pre-weighed beaker.PROCEDURE A ) Extraction 1. 13. 5mL of 3 M NaOH solution was added to decompose the borate ester.20 grams of sodium borohydride was added to the above solution. 12. b) observation test 17. The cyclohexanone was transferred to a large test tube which contained 5mL methanol. 0. 15. 8. 11. The percentage yield of the product were calculated. The product were tested with a fw drops of potassium dichromate . 6. 1.clear upper layer. 3. The test tube was removed from the ice bath and was allowed to stand at room temperature for 10 minutes after a vigorous reaction were occured . The residue were cooled at room temperature and were weighed. The two dichloromethane extact was combined with the small product layer. 5. 9. The product were separated as a small . The remainder of the product from the reaction mixture were extract with two 2 mL portions od dichloromethane. 14. The product were removed as much as possible by usind Pasteur pipette and were placed in a test tube. The solution were transferred to a small dry pre-weighed test tube contained boiling chips by using a pipette. 2. The combined extracts were dried with anhydrous sodium sulfate for a few minutes. 7. . The mixture was cooled in an ice bath. 10. 4mL of water was added to the resulting cloudy solution. The dicholromethane were boiled off in the hood and the residue were collected. 4.

2027 g Percentage yield = 95.4746 g Table 2: Mass of cyclohexanol obtained Mass Mass of test tube + boiling chip Mass of test tube + cyclohexanol Cyclohexanol 18.11 % .6648 g 2.5 mL cyclohexanone Mass of cyclohexanone 63.1399 g 2.1902 g 65.RESULTS Table 1: mass of cyclohexanone Mass Mass of beaker Mass of beaker + 1.7277 g 21.4122g Mass of sodium borohydride added = 0.

4746 g 98.14 g/ mol = 0.02521 mol = then the mol of cyclohexanol . 1 mol of cyclohexanol = 1 mol of cyclohexanone = since the mol of cyclohexanone was 0.02521 mol Equation of formation cyclohexanol.Test Observation Addition of potassium dichromate The colour change from orange to green CALCULATION Mass of cyclohexanone obtained = 2.4746 g Mol of cyclohexanone = mol Molar mass = 2.

02521 mol x 100.6g/mol Mass = 0.4122 x 100% x 100% 2.5361g The actual mass of cyclohexanol = 2.11% Percent error = (theoretical yield – actual yield) theoretical yield) x 100% .02521 mol Molar mass = 100.4122 g Percent yield of reaction: = (actual yield) theoretical yield Percent yield of reaction: = 2.6 g/mol Mass = 2.02521 mol The theoretical mass for cyclohexanol: Mass = mol x Molar mass Mol = 0.5361 = 95.= 1 x 0.02521 mol = 0.

5361 x 100% = 4.89% DISCUSSION For this experiment.4122) 2. by using an appropriate apparatus.5361 – 2.= ( 2. There are some suggestion that can be done in order to improve the result experiment is by using only a small amount of boiling chips because it will slower the boiling process. it created another error because it hard to do the extraction because the tip of pasteur pipette does not reached the bottom layer .There will be some cyclohexanol that still left in the discarded solution. The actual yield and theoretical yield of cyclohexanol were calculated in order to determine the percentage yield of the compound. Besides that. There were some errors that occurred because the percentage yield almost nearly 100%.For example when the extraction process have been done. Based on the calculation. cyclohexanone are converted by a rection with sodium borohydride . use the appropriate apparatus so that all the layers can be extracted smoothly. so it hard to identify and to extract the layer.Next is.the error occured because the colur of the layer was about the same.The other best method in reduction of cyclohexanone were. There must be some of the layers that did not being separated by the Pasteur pipette. Firstly is when the extraction of aquoes solution occured at second and third titration . The mechanism for this reaction is shown below : . instead using basic solution we also can used acidic medium. the percentage yield that had obtained was 95. by using a large test tube.11%.

It indicates that the alcohol was oxidized to form a ketone. The orange colour of the solution will turn to green if there is the present of alcohol. CONCLUSION 1.Potassium dichromate. Cyclohexanone was be reduced to cyclohexanol by sodium borohydride in basic solution REFERENCES: . K2Cr2O7 was used in the confirmation test of the present of alcohol.

2. CA 94002-3098.(7th ed) Brooks/Cole.org/wiki/reduction QUESTIONS 1.(2009) .org/wiki/cyclohexanone 4. http://en.1. http://en. Belmont.wikipedia.org/wiki/sodium borohydride 3. Reduction of 2-butanone . USA. http://en.Organic Chemistry.wikipedia. 10 Davis Drive.wikipedia. John McMurry.what products ddo you expect if you reduce 2-botanone and 3-pentanone with NaBH4 in methanol.

CH3OH. NaOH 2.Compare the reductive abililities of lithium aluminium hydride with those of sodium borohydride NaBH4 Cannot reduced ester to alcohol LiAlH4 Can reduced ester to alcohol Can reduced C=C to C-C Cannot reduced C=C to C-C Can reduced carboxylic acid to alcohol Cannot reduced carboxylic acid to alcohol . CH3OH.NaB H4 H2O. NaOH Reduction of 3-pentanone NaB H4 H2O.

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