CHM 556

ORGANIC CHEMISTRY II
EXPERIMENT 2: SODIUM BOROHYDRIDE REDUCTION OF
CYCLOHEXANONE

NAME
AMAR SAFWAN BIN MOHD ALI HANAPIAH (2015272222)
LAB PARTNER
SALMA IZZATI BINTI SINAR MASHURI (2015839778)
NURUL SHAZREENA BINTI ZULKAFLY (2015258246)
CLASS: AS2453D1
LECTURES NAME: PN. NUR VICKY BIHUD

LABORATORY REPORT MARKING SCHEME

Objective of the Experiment

Introduction
Experimental Procedure
Results and Observations
Calculations
Discussion
Conclusion
Answers to Questions
References
Pre-laboratory preparations
Laboratory techniques
Total Marks

Full
Mark(s)
1.0
2.0
1.0
3.0
3.0
2.0
1.0
3.0
1.0
2.0
1.0
20

Marks
(to be filled by lecturer)

Objective
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 (cyclohanol) obtained.

Introduction
In organic chemistry, a ketone is a compound with the structure RC (=O) R, where R
and R can be variety of atom and groups of atoms. It features a carbonyl group (C=O)
bonded to two other carbons atoms. 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 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 selfassociate and are more volatile than alcohol and carboxylic acids of comparable molecular
weights.
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. 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 (NaBH4). Cyclohexanone and cyclohexanol are the organic compound
with the formula (CH2)5CO and C6H12O respectively.

Experimental procedure
1. The 5ml of methanol is placed in a large test tube, and then 2ml of cyclohexanone is
added into the test tube. The test tube was cooled in an ice bath.
2. 200mg sodium borohydride were carefully added into the solution. After the rigorous
reaction has ceased, the test tube were removed from ice bath and stand at room
temperature for 10 min.
3. 5ml of 3M NaOH solution were added to the solution to decompose the borate ester.
Then 4ml of water were added.
4. The product was separated as a small, clear upper layer. The clear upper layer was
transferred using a Pasteur pipette to another clean test tube.
5. The remainder of the product was extracted from the reaction mixture using two 5ml
of portion of dichloromethane.
6. The dichloromethane extract was combined with the earlier product layer and dry
with anhydrous sodium sulphate.
7. The solution was transferred into a small clean pre weighed round bottomed flask and
the dichloromethane was evaporated using rotoevaporator.
8. The flask was reweighed and the percentage yield of product was calculated.
9. The IR spectrum was obtained.

Result and observation

Mass cyclohexanone
Mass (g)
0.2606
51.6163
17.3437
71.8207

Sodium borohydride
Empty round bottom flask
Stopper
Round bottom flask + stopper +
cyclohexanone
cyclohexanone

2.8607

Mass cyclohexanol
Mass (g)
0.2606
51.6163
17.3437
71.5007

Sodium borohydride
Empty round bottom flask
Stopper
Round bottom flask + stopper +
cyclohexanol
Cyclohexanol

2.5407

Calculation:
Mass of cyclohexanone obtained: 2.8607 g
Mole of cyclohexanone = mass / m.mass
= 2.8607 g / 98.14 g/mol
= 0.0291 mol
1 mol of cyclohexanol = 1 mol of cyclohexanone
Thus, mole of cyclohexanol is 0.0291 mol
Mass of cyclohexanol obtained: 2.5407 g
Theoretical mass of cyclohexanol:
= mole m. mass
= 0.0291 mol 100.6 g/mol
= 2.9275 g

Percentage yield of cyclohexanol = (actual mass / theoretical mass) 100

= (2.5407 g / 2.9275g) 100
= 86.79 %
Observation
The solution of methanol and cyclohexanone react vigorously when added wih
sodium borohydride. The solution turned o pale yellow in colour after the reaction.
The small porion and clean upper layer formed after the addition of 5ml, 3M of
sodium hydroxide and 4ml of water.

Discussion

The purpose 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 powerful nucleophiles that attack
the electrophile and replaces the leaving group in electrophilic carbon. The mechanism of
chemical reaction is as show below;

The hydride nucleophile from NaBH4 attack only electrophilic carbon. In the first
step, the hydrogen H+ detaches from 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 2.5407 g and the theoretical value is
2.9275 g. thus, the percen yield is 86.79 %. Based on the percent yield, the percent is
good but there have a small error during the experiment. The amounts of chemical were
taken probably does not measured accurately. Other than that, maybe there is a
contaminant in the solution.
Based on the IR spectrum analysis, the absorption band for alcohol (OH) bond is at
3367.86 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.

Conclusion
The reduction reaction of cyclohexanone was performed and the expected product
was obtained which is cyclohexanol. The mass of product obtained is 2.5407 g and the
calculated theoretical value is 2.9275 g. the percent yield is 86.79 %. The IR spectrum
analysis was shown that there is an alcohol in the final product.

References

Pavia, D. L. (2005). Introduction to Organic Laboratory Techniques: A Small Scale

Approach. United State of America: Quebecor World Tauntom.
John McMurry, (2009). Organic chemistry brooks/cole, 10 Davis Drive, Belmont, CA 940023098, USA
http://en.wikipedia.org/wiki/sodium-borohydride
http://en.wikipedia.org/wiki/cyclohexanone