Objective

Introduction
Experimental
Procedure
Results and
Observation
Calculation
Discussion
Conclusion
Questions Answer
Reference
Total Marks

Marks
Allocat
ed
1
2
2

Marks

4
4
2
1
3
1
20

FACULTY OF APPLIED SCIENCES

LABORATORY LAB REPORT
ORGANIC CHEMISTRY (II)
Experiment 2 : Sodium Borohydride Reduction of Cyclohexanone
Name : Mohd Nakirudin bin Muhamad Nor
Students ID : 2014595967
Program Code : AS202
Course Code : CHM556
Partners Name : 1)
2)
Date Of Experiment : 21st March 2016
Date of Submission : 28th March 2016
Objective

1. To investigate the reduction of a Ketone to an Alcohol by using Sodium

Borohydride as The Reducing Agent.
Introduction
In organic chemistry, carbonyl reduction is the organic reduction of
any carbonyl group by a reducing agent. Typical carbonyl compounds
are ketones, aldehydes, carboxylic acids, esters, and acid halides. Carboxylic acids,
esters, and acid halides can be reduced to either aldehydes or a step further
to primary alcohols, depending on the strength of the reducing agent; aldehydes
and ketones can be reduced respectively to primary and secondary alcohols. In
Deoxygenation analysis, the alcohol can be further reduced and removed altogether
(Dr Peter,2007). The relatively weak reducer sodium borohydride is typically used
for reducing ketones and aldehydes because unlike lithium aluminum hydride, it
tolerates many functional groups (nitro group, nitrile, ester) and can be used with
water or ethanol as solvents (Albretch, 2011). Lithium aluminum hydride and other
strong reducers such as diisobutylaluminium hydride, L-selectride, diborane,
diazene, and aluminum hydride can also reduce aldehydes and ketones, but are
disfavored because they are hazardous and violently reactive. However, these
compounds are useful for reducing carboxylic acids and esters to alcohols, since
sodium borohydride is not powerful enough to do so ( Dr Peter, 2007).
NaBH4
CH3OH

Figure 1 : Structure of
Cyclohexanone and
Cyclohexanol

Experimental
Procedure

In order to synthesis Cyclohexanol from Cyclohexanone, a series of technique is

applied. 2.0 mL of cyclohexanone was obtained and placed in a small pre-weighed
Round Bottom Flask. The

cyclohexanone

tube

5mL methanol. The mixture was cooled in an ice bath.

which

contained

was

transferred

to

large

test

0.20 grams of sodium borohydride was added to the above solution. 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 occurred. 5mL of 3 M NaOH solution was
added to decompose the borate ester. 4mL of water was added to the resulting
cloudy solution. The product was separated as a small, clear upper layer. The
product was removed as much as possible by using Separatory Funnel and were
placed in a test tube. The remainder of the product from the reaction mixture were
extract with two 5 mL portions of dichloromethane. The two dichloromethane
extract was combined with the small product layer. The combined methylene
chloride layer was dried using anhydrous Sodium Sulphate. Dried methylene
chloride solution was transferred into a pre-weighed small round bottomed flask and
evaporated off the solvent using the rotary-evaporator and IR spectrum was
obtained.

Results and Observation

Mass of Empty Round Bottom Flask (g)
Mass of Cyclohexanone (g)
Mass of Cyclohexanol (g)
Mass of Round Bottom Flask (after

: 56.9596
: 0.2077
: 3.4006
: 60.3602

being rotavaporised) (g)

Table 1: Mass of Chemicals and Apparatus being used.

It is observed that during the separation of organic layer and inorganic layer in
separatory funnel, the clear white layer is observed to be less dense compare to
yellowish-cloudy solution at the bottom layer.
Calculation

Discussion

Ketone is actually a compound with the structure RC(=O)R', where R and R' are
variety of atoms and groups of atoms (Albretch, 2011). In this experiment,
cyclohexanone was reduced to cyclohexanol by sodium borohydride (NaBH4).
Sodium borohydride, also known as sodiumtetrahydridoborate, is an inorganic
compound with the formula NaBH4. 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 is

The IR is furthered analyzed, From the IR Spectrum, it is found that there is still C=O
presenced in the compound at 1708.75 cm-1. This is due to the Cyclohexanone is not
fully synthesized to Cyclohexanol. There is no indicator showing that where is the
right time in order to stop the reaction. Although the separation is observed to bring
Carbonyl in the final product, still the separation is considered to be good, since a
lot of peak can be observed at the IR Spectrum. We can observed that the is -CH 2
(sp3 hybridized Carbon), which the bond being stretched at the wavelength of
2929.53 cm-1 (Albretch, 2011), and at 2858.03 cm-1 (Albretch, 2011). The product
formed also verified and confirmed to be an alcohol, since it is found that at
3597.18 cm-1 (Albretch, 2011), one bond between two atoms is observed to be
present (-O-H). It is clearly show that, 3597.18 cm -1 (Albretch, 2011) belongs to O-H
bond. Other than that, C-O (sp3 hybridized Carbon) is also observed to be presence

at 1138.44 cm-1 (Albretch, 2011). at Stretch condition. Hence, the product

presenced is observed to be an Alcohol compound, with a trace analysis of C=O.

Conclusions
2 : Mechanism
of
From theFigure
experiment,
by performing
a series of technique, a compound which have
Cyclohexanone
the C=O functional
groupto
can be reduced to form an alcohol. In this experiment,
Cyclohexanol (draw by

Cyclohexanone is converted into Cyclohexanol can be reduced by using Sodium

using

Borohydride in Methanol.
www.emolecules.com)

Reference
1. http://www2.ups.edu/faculty/hanson/Spectroscopy/IR/IRfrequencies.html
2. https://en.wikipedia.org/wiki/Carbonyl_reduction
3. Norman L. Allinger and Ernest L. Eliel, James R. Boone and E. C. Ashby Topics
in Stereochemistry, Volume 11, Complex Metal Hydrides: Composition in
Solution and Mechanism of Ketone Reduction, Print ISBN: 9780471054450,
Online ISBN: 9780470147207
4. Dr. Peter I. Dalko, Pavel Koovsk and Andrei V. Malkov, Enantioselective
Organocatalysis: Reactions and Experimental Procedures, DOI:
10.1002/9783527610945.ch7
5. Prof. Dr. Albrecht Berkessel and Dr. Harald Grger, Asymmetric
Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric
Synthesis, Chapter 11, Reduction of Carbonyl Compound (Print ISBN:
9783527305179 Online ISBN: 9783527604678 )