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Soduim Borohydride Reduction of Cyclohexanone
Soduim Borohydride Reduction of Cyclohexanone
CHEMISTRY II
CHM556
EXPERIMENT 2
SODUIM BOROHYDRIDE REDUCTION OF CYCLOHEXANONE
NAME:
(MELLISA ANASTASHIYA)
2013727337
PARTNERS NAME:
LESSIE ANNE JOSEPH
DATE OF EXPERIMENT:
09TH OCTOBER 2014
DATE OF SUBMISSION:
16TH OCTOBER 2014
EXPERIMENTAL PROCEDURE
53.2566
58.1425
54.4517
Weight of cyclohexanol, g
= ( 54.4517 - 53.2566 )
= 1.1951
Theoretical value, g
1.9330
Actual value, g
1.1951
CALCULATIONS
Cyclohexanone, C6H10O
1.1951
1.9330
= 61.8 %
DISCUSSION
The hydride nucleophile from NaBH4 attack only electrophilic carbon. In the
first step, the hydrogen H + detaches from the 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 1.1951g and the theoretical
value is 1.9330g. Thus, the percent yield is 61.8%. Based on the percent yield,
the percent is quite small due to some errors. The amount of chemicals were
taken probably does not measured accurately. Other than that, may be there is a
contaminant in the solution.
Based on the IR spectrum analysis, the absorption band for the alcohol (OH)
bond is at 3368.46 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 (Joseph,
2006). The spectrum also shown the sp3-hybridized CH absorption bands which
is at 2855.01 cm-1 . It is also show a strong band for the CO bond in the 13001000 cm-1 region, although this absorption is difficult to identify because it occurs
in the fingerprint region with many others bands. However, in the spectrum there
is still a carbonyl group band was detected which is at 1646.95 cm -1, this is
because of the errors that have been mentioned above.
CONCLUSION
QUESTIONS
1. What products do you expect if you reduce 2-butanone and 3-pentanone with
NaBH4 methanol.
Reduction of 2-butanone
Reduction of 3-pentanone
2. Compare the reductive abilities of lithium aluminum hydride, LiAlH 4 with those
alcohol
Cannot reduced ester to alcohol.
REFERENCES
Joseph,M.Hornbck. (2006). Organic chemistry, 2nd edition. University of Denver
: physical sciences.
Donal L. Pavia ; Randall G Engel. (2013). Approach to organic laboratory
techniques, 5th edition : Belmont/Cole.
Laboratory techniques:
The techniques involved are;
1. Extraction
2. Separation
3. Distillation
4. Evaporation
5. IR analysis