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ORGANIC

CHEMISTRY II
CHM556
EXPERIMENT 2
SODUIM BOROHYDRIDE REDUCTION OF CYCLOHEXANONE
NAME:
(MELLISA ANASTASHIYA)
2013727337
PARTNERS NAME:
LESSIE ANNE JOSEPH
DATE OF EXPERIMENT:
09TH OCTOBER 2014
DATE OF SUBMISSION:
16TH OCTOBER 2014

UNIVERSITI TEKNOLOGI MARA


UiTM SHAH ALAM
FACULTY OF APPLIED SCIENCE

OBJECTIVE OF THE EXPERIMENT


1. To investigate the reduction reaction of a cyclohexanone to a cyclohexanol by

using the sodium borohydride as the reducing agent.


2. To determine the percent yield of product ( cyclohexanol ) obtained.
INTRODUCTION
Nucleophilic substitution is one of the important reaction when dealing with
carbonyl group. Nucleophilic substitution reaction occur at sp3-hybridized carbon,
which is the nucleophile replaces a leaving group bonded to the electrophilic
carbon. The carbon said to be electrophilic when the leaving group that bonded
to the carbon is being more electronegative. Thus, carbon of a carbonyl group is
an electrophilic due to the electronegativity of the oxygen.
The carbonyl group can be reduce to alcohol by addition of hydride and
perform the nucleophilic substitution, since hydride is a powerful nucleophile and
gives irreversible reaction (Joseph, 2006). Reduction can be defined as a
decrease in the oxygen content or an increase in the hydrogen content of a
compound.
In this experiment, cyclohexanone reduce to cyclohexanol by using the
reducing agent sodium borohydride (NaBH 4). Cyclohexanone and cyclohexanol
are the organic compound with the formula (CH 2)5CO and C6H12O respectively.

EXPERIMENTAL PROCEDURE

The experiment was started with 5 ml of methanol which were placed in a


large test tube,then added with 2 ml of cyclohexanone. The solution was allowed
to cool in an ice bath.
200 mg sodium borohydride was added to the solution with care. The test
tube was removed from ice bath after the vigorous reaction has ceased and
allowed to stand at room temperature for 10 minutes. 5 ml of 3M NaOH was
added into the solution to decompose the borate ester, then added by 4 ml of
water.
The solution allowed to separate into two layer which is the upper layer
should be a small and clear layer that appeared as product. Then, the product
was transferred in a clean test tube by using a Pasteur pipette.
The remainder of the product from the reaction mixture was transferred in a
separatory funnel. Two 5 ml portion of dichloromethane was added into the
separatory funnel to extract the mixture.
The dichloromethane extract was combined with the earlier product layer and
dried with anhydrous sodium sulphate. Then, it was transferred into a small
cleaned pre weighed round bottomed flask and evaporated by using the rotary
evaporator. The weight of flask was taken before and after evaporated. The IR
spectrum for the product was obtained by using liquid sampling technique.

RESULTS AND OBSERVATIONS


Table 1.0 : tabulation of data obtained

Weight of empty flask, g

53.2566

Weight of flask and product before


evaporated, g

58.1425

Weight of flask and product after


evaporation, g

54.4517

Weight of cyclohexanol, g

= ( 54.4517 - 53.2566 )
= 1.1951

Theoretical value, g

1.9330

Actual value, g

1.1951

The result for IR spectrum shown in diagram 1.1.


Observations:
The solution of methanol and cyclohexanone react vigorously when added
with sodium borohydride. The solution turned to pale yellow in colour after the
reaction.
The small portion and clear upper layer formed after the addition of 5ml, 3M
of sodium hydroxide and 4ml of water.

CALCULATIONS
Cyclohexanone, C6H10O

Density = 0.9478 g/ml


Volume = 2ml
Mass = 0.947g/ml x 2ml
= 1.8956 g
Molar mass = 98.15 g/mol
1.8956 g
No. Of moles = 98.15 g/mol
= 0.0193 moles
No. Of moles of cyclohexanol = no. Of moles of cyclohexanone = 0.0193 moles
Molar mass of cyclohexanol = 100.158 g/mol
Theoretical mass of cyclohexanol = no of moles x molar mass
= 0.0193 moles x 100.158 g/mol
= 1.9330 g
Therefore,
Actual
Percent yield % = Theoretical
=

1.1951
1.9330
= 61.8 %

DISCUSSION

The purposes of the experiment are to investigate the reduction reaction of a


cyclohexanone to a cyclohexanol by using the sodium borohydride as the
reducing agent and to determine the percent yield of product (cyclohexanol) that
obtained. Cyclohexanone is a carbonyl group that acts as electrophilic with high
electronegativity of oxygen atom bonded to the carbon. In order to reduce the
cyclohexanone to the cyclohexanol, it is needed to use the addition of hydride to
the solution, because hydride is a powerful nucleophile that attacks the
electrophile and replaces the leaving group in electrophilic carbon. The
mechanism of chemical reaction is as shown below;

The hydride nucleophile from NaBH4 attack only electrophilic carbon. In the
first step, the hydrogen H + detaches from the BH4 and added to the
cyclohexanone which is forms the C-H bond and breaks the C-O bond, resulting
in new lone pair on the oxygen that makes the oxygen negatively charged
( called as alkoxides ). The proton from methanol is added to the alkoxides to
form the cyclohexanol.

The mass of cyclohexanol that was obtained is 1.1951g and the theoretical
value is 1.9330g. Thus, the percent yield is 61.8%. Based on the percent yield,
the percent is quite small due to some errors. The amount of chemicals were
taken probably does not measured accurately. Other than that, may be there is a
contaminant in the solution.

Based on the IR spectrum analysis, the absorption band for the alcohol (OH)
bond is at 3368.46 cm -1 and the band is broad compared to others bands in the
spectrum since alcohols are characterized by a strong and very broad absorption
in the 3550-3200 cm-1 region due to the hydrogen bonded OH group (Joseph,
2006). The spectrum also shown the sp3-hybridized CH absorption bands which
is at 2855.01 cm-1 . It is also show a strong band for the CO bond in the 13001000 cm-1 region, although this absorption is difficult to identify because it occurs
in the fingerprint region with many others bands. However, in the spectrum there
is still a carbonyl group band was detected which is at 1646.95 cm -1, this is
because of the errors that have been mentioned above.

CONCLUSION

The reduction reaction of cyclohexanone was performed and the expected


product was obtained which is cyclohexanol. The mass of product obtained is
1.1951g and the calculated theoretical value is 1.9330g. The percent yield is
61.8%. The IR spectrum analysis was shown that there is an alcohol in the final
product.

QUESTIONS
1. What products do you expect if you reduce 2-butanone and 3-pentanone with
NaBH4 methanol.
Reduction of 2-butanone

Reduction of 3-pentanone

2. Compare the reductive abilities of lithium aluminum hydride, LiAlH 4 with those

of sodium borohydride, NaBH4 .


sodium borohydride, NaBH4

lithium aluminum hydride, LiAlH4

Cannot reduced C=C to C-C

Can reduced alkene to alkane

Cannot reduced carboxylic acid to

Can reduced carboxylic acid to alcohol

alcohol
Cannot reduced ester to alcohol.

Can reduced ester to alcohol.

REFERENCES
Joseph,M.Hornbck. (2006). Organic chemistry, 2nd edition. University of Denver
: physical sciences.
Donal L. Pavia ; Randall G Engel. (2013). Approach to organic laboratory
techniques, 5th edition : Belmont/Cole.
Laboratory techniques:
The techniques involved are;
1. Extraction
2. Separation
3. Distillation
4. Evaporation
5. IR analysis