Reducing aldehydes and ketones to alcohols can be done using different reagents.

One of the
most popular is using hydrogen as a catalyst to produce the alcohol, but in the experiment sodium
borohydride is used as an alternate reagent. The production of 9-fluorenol is done by reducing the 9fluorenone by sodium borohydride, and is the main goal of this experiment. After the production of the
final product it is to be identified using melting point and IR spectroscopy.
Reduction is a reaction in chemistry that involves gaining electrons. If a compound contains a
double bond, it can be reduced by adding hydrogen across the pi bond causing the compound to become
saturated. When reducing carbonyl compounds in a lab it is usually done by using hydrogen because it is
catalytic, therefore it can be reisolated, and used again multiple times. However, it is highly flammable so
it is dangerous to use in a teaching lab. Instead a metal hydride reducing agent is used such as LiAlH 4 or
NaBH4. This is done by producing a hydride ion H-, which causes an addition of electrons, therefore
reducing the molecule. The biggest concern when involving the H- is H+, this is because the reducing
agent will react with proton sources. The largest source of protons is the solvent, so a solvent must be
chosen that cannot protonate the reducing agent. We do not use MeOH with the LiAlH4 because it will
protonate the reducing agent, however it can be used with the NaBH4. The main difference between the
two molecules is that although they are in the same group, aluminum is number 13 and boron is 5
meaning that aluminum is a bigger atom. Because it is a bigger atom, the valence shell electrons are
further from the nucleus, meaning that the electrons are not as tightly bound to the atom as they are with
the boron. This makes boron a weak reducing agent, but useful because unlike LiAlH4 it can be used with
MeOH. Lithium aluminum hydride is not very selective because it highly reactive, which means that it
can reduce things such aldehydes, ketones, carboxylic acids, or even ester and amides. On the other hand
NaBH4 is not very reactive, making it much more selective, which means it can only reduce aldehydes
and ketones into alcohols. Through their difference in selectivity it allows NaBH4 to be used with MeOH
which gives it the ability to carry out reductions when there are other functional groups on a molecule. In
the experiment the transfer of the hydride ion from the borohydride to the electrophilic carbonyl carbon
(carbon is electrophilic because of the electronegativity of the oxygen atom, which makes the carbon
partially positive) of 9-fluorenone occurs at the same time that the boron atom transfers to the carbonyl
oxygen atom. Boron has 4 hydrogens attached to it, and when it is transferred it creates a borate salt
intermediate. Once water and acid are added it cleaves the B-O bond to create 9-fluorenol by the
hydrolyzation of these bonds (water can do this by itself, but acid hastens the process). This is the reason
that 1 molecule of NaBH4 is able to reduce up to 4 molecules of 9-fluorenone at one time. This process is
easily seen in the experiment because 9-fluorenone is very yellow, and 9-fluorenol is white. After the
sodium borohydride dissolves in the solution it should become clear. The following step is the addition of
sulfuric acid, which is added in an apparatus for heating reflux; this step is done until all the solids
dissolve. Once the solids dissolve the solution was allowed to cool to room temperature and then added to
an ice bath until a precipitant formed. The product was then isolated by vacuum filtration followed by
being washed with water until the filtrate was neutral and then allowed to air-dry. There are a couple of
things that were addressed to make sure that the reaction was able to go smoothly, the first being the
amount of NaBH4 to use. In the lab there were many students using the NaBH4, so when the bottle is
repeatedly opened it is exposed to the air, which contains humidity. The more that the NaBH4 gets
exposed to air, the more protonated, and useless it becomes. This was fixed by instead using 20mg of the
NaBH4 to make sure that there was a sufficient working amount for the experiment. Once a crude product
was formed, the next step was to recrystallize it. The first step is to dissolve the product in methanol, this
is done by placing the tube into a water bath (distilled water), and then bringing it to a boil. The reason it
is done in a distilled water bath is because once the product is dissolved water has to be added dropwise,
but it must be added at the same temperature as the methanol. The water is added dropwise until the

solution becomes partly cloudy, this meant that it was ready to be left to cool down and then form a
precipitant, which is then allowed to air-dry. The reason that two different chemicals are used for the
recrystallization is because no single chemical meets the criteria for a good solvent; these criteria are
The purpose of the experiment was to reduce the 9-fluorenone to 9-fluorenol by utilizing sodium
borohydride as a reducing agent. In order to confirm this the product, the melting point and IR
spectroscopy data was analyzed and compared to the actual melting point and IR of the 9-fluorenol. After
the mass of the purified product was determined (.330g of 9-fluornenol), the percent yield was found to
be 55%. A possible reason that this was the percent yield is because some of the product fell off the filter
paper when it was being transferred to a weigh boat, and because this was a microscale procedure any
amount of loss of product greatly affects the percent yield. The melting point was determined to be
around 150-156 degrees Celsius, which is close the actual melting point range of 152-158 degrees
Celsius. The reason that there may have been a difference in the melting point ranges might be because
there were still some impurities in the product. The last thing that was analyzed to determine that the
product was 9-fluorenol was the IR spectrum. In the IR spectrum there is a hydroxyl group broad peak
around 3000-3300 cm^-1, and there was no carbonyl peak in the spectrum, which is a good indication that
the ketone in 9-fluorenone was properly reduced to an alcohol