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George Pappas
In contrast to the organic oxidation reaction - involving the addition of a bond between
carbon and oxygen an organic reduction reaction is characterized with a loss of a bond between
carbon and oxygen. In order to lose a bond for a reduction reaction, one would use a reducing
agent that would add a hydride to the reactant. A nucleophile is a compound that has excess
electron density, further allowing it to donate a hydrogen. With that said, the more desirable
reducing agent would be one that is also considered a good nucleophile. A nucleophilic addition
would further donate a hydride to the reactant, and further reduce the amount of bonds between
carbon and oxygen. Similar to the organic oxidation reaction, a reduction reaction is very
dependent on its reducing agent. Considering the strength of the reducing agent, will further
determine the number of bonds between carbon and oxygen. For instance, a strong nucleophilic
reducing agent as well as a strong base, like Lithium Aluminum Hydride, is capable of reducing
a carboxylic acid to a primary alcohol, it concludes with no reaction due to the strength of the
reducing agent.
in the reactant, the experiment will result with two products cis and trans products. In
conclusion, the two products will be further analyzed to determine which is a kinetic product and
Experimental Section
Added 1.5ml
Cool mixture Took a TLC (using
methanol and 0.299g Placed it in iodine
in ice bath in 1ml Ethyl Acetate
2- chamber (Found
small beaker and 4ml Hexane)
Methylcyclohexanone Rf for ketone)
of this mixture
into 5ml vial
Reweighed
product and
found % yield
Table of Chemicals
Obtained IR and
HNMR spectrum.
Methanol CH30H
MM: 32.04g/mol
MP: -97.6C
BP: 64.7C
Iodine I2
MM: 253.81g/mol
MP: 113.7C
BP: 184.4C
Dichloromethane CH2Cl2
MM: 84.93g/mol
MP: -96.7C
BP: 39.6C
Hexane C6H14
MM: 86.18g/mol
MP: -95.35
BP: 68.73C
Ethyl Acetate C4H8O2
MM: 88.11g/mol
MP: -83.6C
BP: 77.1C
Sodium Sulfate Na2SO4
MM: 142.04g/mol
MP: 884C
BP: 1429C
2-Methylcyclohexanone C7H12O
MM: 112.17g/mol
MP: -14C
BP: 162.1C
Sodium Borohydride NaBH4
MM: 37.83g/mol
MP: 400C
BP: 500C
Sodium Hydroxide NaOH
MM: 39.997g/mol
MP: 318C
BP: 1388C
Results
Chart 2:
Rf product: 0cm = 0 cm
4cm
characteristic of the product was that it was a translucent oil. The product resulted with a weight
of 0.319g which is the weight the experiment began with. This further led to the percent yield to
be 100%. Most likely there were possible errors that occurred, further causing the percent yield
to be exactly 100%. Possible errors include not evaporating all of the solvent, or not separating
the aqueous layer from the organic layer accurately. Incomplete drying of the organic layer could
have acted as another error that could have caused the percent yield to be as high as it concluded
to be.
Performing a TLC of the reaction helped determine whether or not the reaction was
complete. With the beginning Rf value standing at 0.575 cm and the final Rf value at 0 cm, the
experiment was successfully reduced and concluded. In more detail, analyzing the difference in
the location of the spot on the TLC plate aided in indicating whether the reaction was complete
or not. With that said, as the spot decreased from its original position to the base line, it was
While TLC aided in clarifying if the reaction was complete or not, the IR spectrum acted
as an indication to whether or not the desired product was obtained at the end of the experiment.
In this experiment a ketone was simply reduced to a secondary alcohol. The IR spectrum in
Figure 4 for 2-Methylcyclohexanone depicted a sharp peak near 1710 cm-1 implying that a
carbonyl possibly a ketone is present. Sharp peaks slightly up-field from 3000 cm-1 indicated
that hydrocarbons are in this compound as well. In contrast, the IR spectrum in Figure 3 for 2-
Methylcyclohexanol magnifies that an alcohol is produced. The large, round peak near 3400
cm-1 clarifies that there is an alcohol present. The sharp peaks between 2700 cm-1 and 2900 cm-1
illustrate hydrocarbon bonds. Overall, the IR spectrum of the final product obtained, revealed
that the desired product was attained as it included the same characteristics in that of the
HNMR would have additionally aided in identifying the product. This spectrum goes
more into detail as it shows the difference between the two isomeric products attained from this
reduction reaction. HNMR makes it possible to figure out how many hydrogens are present and
where they are located by analyzing the given peaks. Considering that the objective is to
differentiate between the two isomers, HNMR would indicate which is the cis compound and
which is the trans by looking closer into the characteristics of the hydrogens. Overall, HNMR
aids in looking for the number of signals, position of each signal, splitting patterns, and the
integral to further help in differentiating between two similar compounds. In this particular
scenario, the cis compound would most likely show a greater coupling value than the trans
Conclusion
As stated previously, in order for a reduction reaction to succeed, the starting compound
must lose a bond between the carbon atom and oxygen atom. In this particular experiment, 2-
oxygen and a carbon was lost. This further reflects the theory stated above.
Reduction reactions can be found outside of the laboratory as well. In recovering metals,
sodium borohydride is used to reduce metal ions back into their free metal state. This further aids
reducing agent NaBH4. Although there might have been errors that conflicted with a proper
Reference