EXPERIMENT 2

SODIUM BOROHYDRIDE REDUCTION

OF CYCLOHEXANONE

NAME : NUR SARAH HANNIS BT KAMARULZAMAN

STUDENT ID : 2019291342
GROUP : AS2453M1
DATE : 10TH NOVEMBER 2020

Objective (1M)

Introduction (2M)

Procedure in flowchart (2M)

Calculation (5M)

Discussion (3M)

Conclusion (1M)

Questions (4M)

References (1M)

Appendix 1 (1M)

TOTAL
 Objectives
i. To synthesize cyclohexanol from the reduction of cyclohexanone using sodium
borohydride, NaBH4
ii. To characterize the reduction product using IR spectroscopy

Introduction
Ketone is a functional group with the structure of 𝑅 − 𝐶 − 𝑅 ′ where R can be any carbon-.

=
containing substituents. Ketone undergoes many
o nucleophilic addition reaction. But
in this experiment, we will be investigating the reduction of ketone to a secondary alcohol
using NaBH4 as the reducing agent. Methanol was used as solvent because NaBH4 is more
soluble in methanol than in ethanol although it can react with both solvent. The ketone that we
will be using for this experiment is cyclohexanone. Below is the reduction mechanism for this
reaction.
 Procedure

5 ml of methanol was and followed by 2 ml of

placed in a large test cyclohexanone. The test
tube using measuring tube was then swirled.
cylinder
200mg of NaBH4 The test tube was cooled
The mixture then was carefully in an ice bath for few
are stirred well added into the minutes
using a glass rod solution

After the rigorous solution has 5 ml of 3M NaOH was added

ceased, the test tube from the into the test tube to
ice bath was let to rest at room decompose burate ester and
temperature for 10 minutes until the test tube was swirled
reaction took place until two layers suspended

The remaining Pasteur pipette was

product was used to transfer as much
The product was
transferred into of the upper layer to
extracted using 5 ml
a separatory another clean 50 ml
of dichloromethane conical flask
funnel

Methanol was added

into the separatory
The separatory The dichloromethane
funnel and
funnel was was combined with
dichloromethane was
then swirled to previous organic layer
separated from the
mix well the
aqueous layer. This step
solution
was repeated twice

Fluted filter paper was used to The bottom layer was

filter the solution and the placed into the organic
solution was transferred into layer and dried with Methanol was
a dry and small round bottom anhydrous Na2SO4 and added to the
flask and evaporate the stir well using glass rod separatory
dichloromethane using rotary funnel and
evaporator swirled
Calculation

1 𝑚𝑜𝑙 1𝑔
Mass of cyclohexanone obtained = 2𝑚𝑙 × ×
98.15 𝑔 1 𝑚𝑙

= 0.0204 𝑚𝑜𝑙
Mole of cyclohexanol = 0.0204 mol
𝑔
Theoretical mass of cyclohexanol = 0.0204 𝑚𝑜𝑙 × 100.158 𝑚𝑜𝑙

= 2.043 𝑔
𝐴𝑐𝑡𝑢𝑎𝑙 𝑚𝑎𝑠𝑠
Percentage yield = 𝑇ℎ𝑒𝑜𝑟𝑖𝑡𝑖𝑐𝑎𝑙 𝑚𝑎𝑠𝑠 × 100%
1.5020𝑔
= × 100%
2.003𝑔

= 73.51%
Discussion
The cyclohexanone was successfully reduced to cyclohexanol when the pale yellow solution
turned into colour. This reaction is a nucleophilic addition reaction that’s uses a strong
nucleophile which is NaBH4 in order to reduce ketone to secondary alcohol. The mechanism
of this reaction is as shown as below

The percentage yield of cyclohexanol was calculate using this formula % 𝑌𝑖𝑒𝑙𝑑 =
𝐴𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
× 100 and the value obtained is 73.52% .
𝑇ℎ𝑒𝑜𝑟𝑖𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
Based on IR spectrum table, the IR data are
Compound Wavenumber (cm-1) Type of bond(group)
Cyclohexanone ~1715 C=O
Cyclohexanol ~3400 C-OH

The IR of a ketone usually has a frequency of ~1705-1725. Based on the IR spectrum of

cyclohexanone, the C=O stretch at ~1715cm-1 while an alcohol usually stretch at higher
frequency which is ~3200-3400cm-1. This is due to O-H being a prominent band. Based on the
IR spectrum, the spectrum of cyclohexanol appears to have broad and intense stretching
indicating a successful reduction.

Conclusion
The percentage yield of cyclohexanol is 73.52%. The IR spectrum showed a broad absorption
at peak ~3400cm-1 belong to an O-H group, shows a successful reduction of ketone to alcohol.

Questions
1. The stretch went from ~1715cm-1 to ~3400cm-1
2. It act as a drying agent to absorb excess moisture in cyclohexanol solution.
3. Yes, because NaBH4 will only react with carbonyl aldehyde or ketone and never carbonyl
of esters or carboxylic acids.

References
Sholes, A & Hudak, N. Reduction of Cyclohexanone with Sodium Borohydride in Aqueous
Alkaline Solution. Retrieved from https://chemistry.missouri.edu/sites/default/files/class-
files/depakote_step_1.pdf
Appendix
i. Cyclohexanone

C=O
stretch

ii. Cyclohexanol

C-OH
Broad
stretch