Objective

To synthesis cyclohexanol from cyclohexanone by using reduction of reaction with

sodium borohydride (NaBH4).
To determine the percentage yields of product produced.

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. The carbonyl group is polar as a consequence of the fact that the
electronegativity of the oxygen centre is greater than that for carbonyl carbon. Therefore,
ketones are nucleophilic at oxygen and electrophilic at carbon because the carbonyl group
interacts with water by hydrogen bonding. It more soluble in water. Ketones are a hydrogenbond acceptors and not usually hydrogen-bond donors because of their inability to serve both
as hydrogen-bond donors and acceptors. It more volatile than alcohols and carboxylic acids of
comparable molecular weights. These factors relate to pervasiveness of ketones in perfumery
and as solvents.

In this experiment, the reduction of a ketone to an alcohol using sodium borohydride as the
reducing agent was investigated. Sodium borohydride (NaBH4), also known as
tetrahydridoborate is an inorganic compound. This white solid, usually encountered as a
powder, is a versatile reducing agent that finds wide application in chemistry (laboratory and
technical scale). Large amounts are used for bleaching wood pulp. The compound is insoluble
in ether, and soluble in glyme solvents, methanol and water, but reacts with the latter two in the
absence of base.
Experimental Procedure :
1. A 5 mL of methanol followed by 2 mL of cyclohexanone were placed in large test tube. The
mixture was cooled in the ice bath and NaBH4 (200mg) was added. A vigorous, bubbling
reaction took place for several minutes.
2. After the reaction ceased, test tube was removed from ice bath and allowed it to cool at
room temperature. 3M NaOH (5 mL) was added to the solution to decomposed the borate
ester, leaving a cloudy solution.
3. Water (4 mL) was added, allowing the product to separate as a mostly clear upper layer in
separating funnel.
4. The layer was removed and transferred it into a clean test tube and then two successive
methylene chloride (5 mL each) additions were used to extract the remaining product (in the
bottom layer).

5. The recovered products were dried using anhydrous sodium sulphate and the methylene
chloride was subsequently boiled away using rotoevaporator. During the boiling, methylene
chloride vigorously formed bubbles and carried some product away.
6. The flask was reweigh and calculate the percentage yield of product (temperature must be
more carefully moderated, or a larger flask must be used).
7. IR spectrum and gas chromatography were conducted with the product.

Result / Observations

Mass Empty Round Bottom Flask

56.3451 g

Mass Round Bottom Flask with Product

57.5414 g

Mass of Product (Cyclohexanol)

1.1963 g

1. The solution of methanol and cyclohexane react vigorously when added with sodium
borohydride.
2. The solution turned to pale yellow in color after the reaction.
3. The solution formed two layer when decompose borate ester which is clear at upper layer
and cloudy at the bottom layer.
4. The solution formed emulsion when been extracted.

Calculation

Molar mass cyclohexanone = 98 g/mol

Molar mass cyclohexanol

= 100 g/mol

Density cyclohexanone

= 0.9478 g/cm3

Volume cyclohexanone

= 2 mL

1) mass of cyclohexanone
2 mL = 2 cm3 , if Density = 0.9478 g/cm3
2 cm3 x 0.9478 g/cm3 = 1.8596 g
2) moles of cyclohexanone
1.8596 g x ( 1 / 98 g/mol ) = 0.0193 mol

3) Theoritical cyclohexanol
0.0193 mol x 100 g/mol = 1.93 g
Therefore, percentage yield of cyclohexanol = ( actual / theoretical ) x 100%
= ( 1.1963 / 1.93 ) x 100%
= 61.98 %

Discussion

This experiment is to synthesis cyclohexanol from cyclohexanone by using reduction of reaction

with sodium borohydride (NaBH4) and to determine the percentage yields of product produced
(cylohexanol).

cyclohexanone

cyclohexanol

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of
six-carbon cyclic molecule with a ketone functional group. It is slightly soluble in water, but
miscible with common organic solvents. Where cylohexanol is organic compound with
the formula (CH2)5CHOH and related to cyclohexane ring by replacement of one hydrogen atom
by a hydroxyl group. In this experiment, based on the IR spectra of product, from the spectrum
can indicate that the reduction of cyclohexanol from cyclohexanone was completed. This is
because, a large valley centred on wavenumber around 3600 cm-1 was there which is for
alcohol (product IR) is 3429.67 cm-1 , and revealed no structure around wavenumber 1750 cm-1
which is showed the presence of ketone structure. 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 61.98 %.

Conclusion

As a conclusion, ketone group (cyclohexanone) can be converted to alcohol group

(cyclohexanol) by using reduction reaction by sodium tetrahydridoborate (NaBH4). In this
experiment, it was highly successful in reducing the ketone group of cyclohexanone to an
alcohol group (cyclohexanol) using sodium borohydride which from the IR spectrum
wavenumber for product (cyclohexanol) is 3429.67 cm-1. Also, the percentage yield of product
prodeuced (cyclohexanol) can be deteremined which is 61.98 %.

Questions / Answers

1) Why do you add sodium hydroxide in your reduction procedure?

Sodium Hydroxide was added in reduction procedure because to decompose the borate
ester. It functions as a base, a ligand, a nucleophile and a catalyst also absorb carbon
dioxide and moisture in the air. It soluble in water, ethanol and methanol. After that, water
was added so it formed two layer where the product separate as a small, clear upper layer.
Benzil treated with sodium borohydride gives the diol hydrobenzoin via a nucleophilic addition
reaction. The sodium borohydride reaction is much less basic than benzil and can run the
reaction in a protic solvent such as ethanol.
2) Why did you use anhydrous sodium sulphate for the above procedure?
Anhydrous sodium sulphate was used to absorb water to dry the product. It is drying agent. In
the laboratory, anhydrous sodium sulfate is widely used as an inert drying agent, for removing
traces of water from organic solutions. It is more efficient, but slower-acting, than the
similar agent magnesium sulfate.
3) Mechanism for the above reduction,

4) During the reaction, why you need to place the test tube onto a beaker containing ice bath?
This is because, during the reaction there will have the splash, so that need to place the test
tube onto a beaker containing ice bath to cool down the reaction and reduce the splash. So, it
was more safety when run the experiment.
5) From your spectrum, indicate either the reduction was completed or not? Give your reason.
In this experiment, based on the IR spectra of product, from the spectrum can indicate that
the reduction of cyclohexanol from cyclohexanone was completed. This is because, a large
valley centred on wavenumber around 3600 cm-1 was there which is for alcohol (product IR)
is 3429.67 cm-1 , and revealed no structure around wavenumber 1750 cm-1 which is showed
the presence of ketone structure.

References

Pavia, Lampman, Kriz and Engel. Introduction to Organic, Laboratory Manual, CHM 260,
2014, 10

Organic Chemistry ll (CHM 556), Note Organic Chemistry ll, 2014, 10

Indian Journal of Chemistry (2006), Reduction Of Carbonyl Compounds With Sodium

Borohydride, Retrieved on 2014, October 11, from www.nopr.niscair.res.in

Reduction of Cylohexanone, 11 October 2014,

http://www2.volstate.edu/chem/2020/Labs/The%20Microscale%20Reduction%20of%20
Cyclohexanone.pdf

Reduction of Cyclohexanone, 13 October 2014,

https://www.scribd.com/doc/36830540/Exp-3-Reduction-of-Cyclohexanone-WithSodium-Borohydride

Datasheet