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Exp 3 Reduction of Cyclohexanone With Sodium Borohydride
Exp 3 Reduction of Cyclohexanone With Sodium Borohydride
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
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
63.1902 g
65.6648 g
Mass of cyclohexanone
2.4746 g
Table 2:
Mass of cyclohexanol obtained
Mass
Mass of test tube + boiling chip
18.7277 g
21.1399 g
Cyclohexanol
2.4122g
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.
(actual yield)
x 100%
theoretical yield
Percent yield of reaction:
=
2.4122
x 100%
2.5361
=
95.11%
x 100%
theoretical yield)
= ( 2.5361 2.4122)
x 100%
2.5361
= 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.
2.
3.
4.
QUESTIONS
1.what products ddo you expect if you reduce 2-botanone and 3-pentanone with NaBH 4 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
LiAlH4
Can reduced ester to alcohol