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.

Sodium tetrahydridoborate is a more gentle (and therefore safer) reagent than lithium tetrahydridoaluminate. It can be used in solution in alcohols or even solution in water provided the solution is alkaline. Solid sodium tetrahydridoborate is added to a solution of the aldehyde or ketone in an alcohol such as methanol, ethanol or propan-2-ol. Depending on which recipe you read, it is either heated under reflux or left for some time around room temperature. This almost certainly varies depending on the nature of the aldehyde or ketone. At the end of this time, a complex similar to the previous one is formed.

In the second stage of the reaction, water is added and the mixture is boiled to release the alcohol from the complex.

Again, the alcohol formed can be recovered from the mixture by fractional distillation. In this experiment cyclohexanone was reduce to cyclohexanol by sodium borohydride (NaBH4).

NaB H4 H2O, CH3OH, NaOH

Mechanism for the above reaction:

PROCEDURE A ) Extraction 1. 1.5 mL of cyclohexanone was otained and placed in a small pre-weighed beaker. 2. The cyclohexanone was transferred to a large test tube which contained 5mL methanol. 3. The mixture was cooled in an ice bath.
4. 0.20 grams of sodium borohydride was added to the above solution.

5. 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 . 6. 5mL of 3 M NaOH solution was added to decompose the borate ester. 7. 4mL of water was added to the resulting cloudy solution. 8. The product were separated as a small ,clear upper layer. 9. The product were removed as much as possible by usind Pasteur pipette and were placed in a test tube.
10. The remainder of the product from the reaction mixture were extract with two 2 mL

portions od dichloromethane,CH2 Cl2 . 11. The two dichloromethane extact was combined with the small product layer. 12. The combined extracts were dried with anhydrous sodium sulfate for a few minutes.
13. The solution were transferred to a small dry pre-weighed test tube contained boiling

chips by using a pipette. 14. The dicholromethane were boiled off in the hood and the residue were collected. 15. The residue were cooled at room temperature and were weighed. 16. The percentage yield of the product were calculated. b) observation test 17. The product were tested with a fw drops of potassium dichromate .

RESULTS Table 1: mass of cyclohexanone

Mass Mass of beaker Mass of beaker + 1.5 mL cyclohexanone Mass of cyclohexanone 63.1902 g 65.6648 g 2.4746 g

Table 2: Mass of cyclohexanol obtained

Mass Mass of test tube + boiling chip Mass of test tube + cyclohexanol Cyclohexanol 18.7277 g 21.1399 g 2.4122g

Mass of sodium borohydride added = 0.2027 g Percentage yield = 95.11 %

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 = 2.4746 g 98.14 g/ mol = 0.02521 mol Equation of formation cyclohexanol.

1 mol of cyclohexanol = 1 mol of cyclohexanone = since the mol of cyclohexanone was 0.02521 mol = then the mol of cyclohexanol

= 1 x 0.02521 mol = 0.02521 mol

The theoretical mass for cyclohexanol: Mass = mol x Molar mass Mol = 0.02521 mol Molar mass = 100.6g/mol Mass = 0.02521 mol x 100.6 g/mol Mass = 2.5361g

The actual mass of cyclohexanol = 2.4122 g

Percent yield of reaction: = (actual yield) theoretical yield Percent yield of reaction: = 2.4122 x 100% x 100%

2.5361

95.11%

Percent error = (theoretical yield actual yield) theoretical yield)

x 100%

= ( 2.5361 2.4122) 2.5361

x 100%

= 4.89%

DISCUSSION

For this experiment, cyclohexanone are converted by a rection with sodium borohydride . The actual yield and theoretical yield of cyclohexanol were calculated in order to determine the percentage yield of the compound. Based on the calculation, the percentage yield that had obtained was 95.11%. There were some errors that occurred because the percentage yield almost nearly 100%. Firstly is when the extraction of aquoes solution occured at second and third titration ,the error occured because the colur of the layer was about the same, so it hard to identify and to extract the layer.There will be some cyclohexanol that still left in the discarded solution. Besides that, by using a large test tube, it created another error because it hard to do the extraction because the tip of pasteur pipette does not reached the bottom layer . There must be some of the layers that did not being separated by the Pasteur pipette. 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.Next is, by using an appropriate apparatus.For example when the extraction process have been done, use the appropriate apparatus so that all the layers can be extracted smoothly.The other best method in reduction of cyclohexanone were, instead using basic solution we also can used acidic medium. The mechanism for this reaction is shown below :

Potassium dichromate, K2Cr2O7 was used in the confirmation test of the present of alcohol. The orange colour of the solution will turn to green if there is the present of alcohol. It indicates that the alcohol was oxidized to form a ketone.

CONCLUSION

1. Cyclohexanone was be reduced to cyclohexanol by sodium borohydride in basic solution

REFERENCES:

1. John McMurry,(2009) .Organic Chemistry.(7th ed) Brooks/Cole, 10 Davis Drive,

Belmont, CA 94002-3098, USA. 2. http://en.wikipedia.org/wiki/sodium borohydride 3. http://en.wikipedia.org/wiki/cyclohexanone 4. http://en.wikipedia.org/wiki/reduction

QUESTIONS 1.what products ddo you expect if you reduce 2-botanone and 3-pentanone with NaBH4 in methanol. Reduction of 2-butanone

NaB H4 H2O, CH3OH, NaOH

Reduction of 3-pentanone

NaB H4 H2O, 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