Reduction of Benzophenone
Christian Concepcion*, Lorenz Diaz*, Justine Kalaw*, and Christian Lagamayo*
College of Science, University of Santo Tomas, Manila, Philippines
ABSTRACT
The main purpose of this experiment is to examine the reductive conversion of
benzophenone to diphenylmethanol. In addition to simply explaining the details of the
reduction reaction, the concept of the limiting reagent and the ways by which the
progress or extent of an organic reaction can be monitored, shall be discussed. The
experiment aims to reduce Benzophenone to Diphenylmethanol using Sodium
Borohydride.
INTRODUCTION
Reduction is the loss of oxygen with the use of a reducing agent, and along with
the loss of an oxygen is the addition of a hydrogen. In this experiment Sodium
Borohydride (NaBH4) is used as a reducing agent for the benzophenone to
diphenylmethanol. The reducing agent will be used in excess to ensure the complete
reduction of the limiting reagent and its carbonyl group. The experiment will start with
the addition of benzophenone in methanol in a round bottomed flask. Because sodium
borohydride is not very soluble in organic solvents, so the reaction is going to be carried
out in the ethanolic aqueous solution. Then after the benzophenone is dissolved in
methanol, add boiling chips and put the flask in an ice bath, while sodium borohydride
over a period of 10 minutes. This is done in an ice bath to slow down the rate of reaction
and to control the amount of heat being released by sodium borohydride (NaBH4). And
this is done until a vigorous formation of hydrogen has stopped. On the next step the
students will be putting the reaction mixture in a reflux setup over a boiling water bath
for about 30 minutes. This is done so that solvent vapors are to be trapped in the
condenser, and the concentration of the reactants in the flask would remain constant
throughout. After refluxing the mixture cool it in ice. After cooling the mixture add
dropwise 6M of HCL to decrease the pH of the mixture and turn the solution into an
acid. Then check the pH of the mixture with litmus for later analysis of the compounds
obtained in the reaction. And after filtration and crystallization of the mixture, a series of
test would be done to identify whether the product yielded is indeed diphenylmethanol.
RESULTS AND DISCUSSION
The reaction of benzophenone with sodium borohydride to form diphenylmethanol is an
example of a sodium borohydride reduction of a ketone to an alcohol. The limiting
reagent in this reaction is benzophenone which is the reactant that is totally consumed
when the reaction is deemed complete. The amount of product formed is limited by this
reagent, since the reaction cannot proceed further when all of this reagent is gone.
Balancing the reaction equation is the first step in calculating the percent yield of the
product in a reaction.
Actual yield
% yield =
T heoretical yield × 100
The amount of product obtained in the experiment is referred to as the actual
yield which will be an important component in presenting a reportage for any reaction.
Using the sample amounts to be used in the reaction, we can calculate the theoretical
yield to be, since benzophenone was the limiting reagent:
Theoretical yield = 0.5g A (1mole A/182.22g) (4moles C/4molesA) (184.24g
C/1mole C) = 0.5055g C
The amount of product obtained in the experiment is referred to as the actual
yield which will be an important component in presenting a reportage for any reaction.
EXPERIMENTAL
Before the start of the experiment the reagents, equipment, and personal
protection equipment were prepared for the experiment which is to be done by the
students. The reagents that is going to be prepared are the following: 2.7g of
benzophenone, 30 ml of methanol, and 0.5g of sodium borohydride. And the equipment
needed are the following: a round bottom flask, ice bath, boiling chips, beaker, a reflux
setup, and separatory funnel.
The first step in the experiment was to dissolve 2.7g of benzophenone in
30ml of methanol in a 100ml round bottom flask. Then add boiling chips and cool the
flask over an ice bath. The next step is to weigh 0.5g of NaBH4 in a 50ml beaker. And it
is to be kept covered until ready to be used. Then with the flask on ice, slowly and
carefully add the sodium borohydride (NaBH4) to the benzophenone over a period of 10
minutes. And wait until vigorous evolution of hydrogen stops before moving on to the
next step of the experiment. After the addition of sodium borohydride the mixture is to
be refluxed over a boiling water bath for 30 minutes. Then cool the mixture in ice and
add dropwise 6M HCL to acidify the solution. After check the pH with litmus. Then after
the reflux the solution is transferred into a separatory funnel and extract twice with the
30ml portions of ether. And wash the ether extracts with 50ml of water and dry the ether
with mixing it on a beaker containing half a spatula of NaSO4. The ether is then
decanted onto a tared evaporating dish and it is to be removed over a steam bath. The
diphenylmethanol product is to be recrystallized using hexane, and then dried in
between filter papers. Then the product is to be weighed and after determine the %
yield. Finally we compare the TLC profile taken from the diphenylmethanol with that of
benzophenone using ethyl acetate-hexane developing solvent. After that take the
melting point and IR profile of the diphenylmethanol and compare it with the starting
benzophenone from step one.
REFERENCES
Clark, J. (2019, June 5). Definitions of Oxidation and Reduction. Retrieved October 19,
2019, from
https://chem.libretexts.org/Bookshelves/Analytical_Chemistry/Supplemental_Modules_(
Analytical_Chemistry)/Electrochemistry/Redox_Chemistry/Definitions_of_Oxidation_and
_Reduction.
Nichols, L. (2019, August 18). 1.3K: Reflux. Retrieved October 19, 2019, from
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book:_Organic_Chemistry_
Lab_Techniques_(Nichols)/1:_General_Techniques/1.3:_Heating_and_Cooling_Method
s/1.3K:_Reflux.
