Professional Documents
Culture Documents
Experiment 2 Sodium Borohydride Reduction of Cyclohexanone
Experiment 2 Sodium Borohydride Reduction of Cyclohexanone
Objective (1M)
Introduction (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
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
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