The Reduction of a Ketone
Reaction Figure 1 - Reaction for the reduction of cyclohexanone
Mechanism
Figure 2 - Mechanism showing the reduction of cyclohexanone
Introduction
The reduction of ketones on an industrial scale allows for the synthesis of many products inclusing some used in the medical field. NaBH4 is used instead of LiAlH4 as it is does not react with hydroxylic compounds as intensely thus making it much more particular with which compounds it reacts. Due discriminatory nature NaBH4 can be used to reduce ketone in a great variety of prevalent functional groups such as those found in nitriles, esters and carboxylic acids. Cyclohexanone and NaBH4 must react in a 4:1 ratio as 1 mol of NaBH4 donates 4 Hydrogen ions for every
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10M×v1=3M×10ml
V1= 3ml
Therefore 3ml of 10M HCl is mixed with 7ml water to create a 3M dilution.
Percentage yield using equation 5:
Theoretical yield= 12.5 g
Actual yield= 5.4879 g 5.4879/12.5×100=43.90%
The final product was a clear, colourless liquid, with an oily consistency, which was the cyclohexanol (5.4879g). Nuclear Magnetic Resonance Spectroscopy
1H NMR δ (600MHz, CDCl3 ) f1 (ppm)
3.57-3.51 (1H, m, H -1)
1.97-1.94 (2H's, m, H - 4; H - 4)
(1.72-1.65) - (1.42-1.34) (8H's, m, H - 2; H - 2; H - 3; H - 3; H - 5; H - 5; H - 6; H - 6)
0.84 (1 H, s, H on -OH )
References http://www.nbs.csudh.edu/chemistry/faculty/nsturm/CHE303L/CarbonylReductionExperiment.htm (05/09/2017) http://www.nbs.csudh.edu/chemistry/faculty/nsturm/CHE303L/CarbonylReductionExperiment.htm (05/09/2017) https://www.boundless.com/chemistry/textbooks/boundless-chemistry-textbook/nonmetallic-elements-21/boron-152/boranes-boron-hydrogen-compounds-590-7246/
We then took 1ml of the 0.1% solution from test tube 2 using the glucose pipette and added it to test tube 3, we then used the H2O pipette and added 9ml of H2O into test tube 3 creating 10ml of 0.01% solution.
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second test tube also add 6 mL of 0.1M HCl. Make a solution of 0.165