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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 C-
C-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.
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.
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.
NaB
H4
H2O, CH3OH,
NaOH
Mechanism for the above reaction:
PROCEDURE
A ) Extraction
2. The cyclohexanone was transferred to a large test tube which contained 5mL
methanol.
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 .
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.
b) observation test
Table 1:
mass of cyclohexanone
Mass
Table 2:
Mass of cyclohexanol obtained
Mass
Cyclohexanol 2.4122g
CALCULATION
Molar mass
= 2.4746 g
98.14 g/ mol
= 0.02521 mol
2.5361
= 95.11%
= 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.
CONCLUSION
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 LiAlH4
Can reduced ester to alcohol