The Grignard Reaction

By
Stephan Shansey, Shanseys@go.stockton.edu
Chem 2125-008
December 9th, 2015
Abstract:
This experiment sought to explore a two step reaction which created benzoic acid. The
reactions theoretical yield was determined to be 264.4mg using a calculation shown below.
Upon completion of the experiment, the recovered product was weighed and determined to be
214mg and through calculation it was found that this recovered product was 81% of the
theoretical yield. Since the reaction yielded 81% of the theoretical value this reaction was
deemed to be efficient.
Purpose/Theory:
The purpose of this experiment was to react bromobenzene with magnesium to form
phenyl-magnesium bromide (the Grignard reagent), which was then reacted with solid carbon
dioxide to form a benzoate ion. After the benzoate ion is made, The addition of aqueous
hydrochloric acid adds the proton to the benzoate ion, givingbenzoic acid (Griffiths, J. et al,
2010). The experiment sought to highlight a two-step reaction and how it is conducted, as well
as introducing a micro scale apparatus and its proper use in the lab. The microscale preparation
is quite a useful way to carry out a reaction, because it reduces exposure to hazardous chemicals
and works to create a faster reaction.
Results and Discussion:
After the experiment was completed and the data was compiled it was determined that a
total of 0.214 grams of benzoic acid was recovered. When compared to the theoretical recovery
this recovered weight was not far off from the theoretical weight of .264 grams. the following
calculation was used to determine the theoretical yield of the product benzoic acid.
340 mg 1mmol BrBz 1 mmolPhMgBr 181.31 mg
1 mlBrB z x
x
x
x
=392.6 mg PhMgBr
1 ml
157.01 mg
1 mmolBrBz
1 mmol
1mmolPhMgBr
1mmolBA
122.12 mg
392.6 mgPhMgBr x
x
x
=264.4 mg BA
181.31 mg
1 mmolPhMgBr
1 mmol
Equation obtained from Dr. Aaron Wohlrab, Chem 2125-008 Lab 9 pre-lab notes.
When the theoretical yield is compared to the actual yield, they are indeed quite close.
Upon further analysis of percent yield it was found that the percent yield was equal to 81%. The
percent yield was obtained using the following equation.
.214 g
%yeild=
x 100
.264 g
In the context of the percent yield and the overall comparison to the theoretical yield the
result of the reaction was a success. Not only was the product of benzoic acid produced, but the
yield was quite high. While if carried out completely correctly with no error on behalf of the
researcher the percent yield would be higher. Overall in the conditions provided in the lab this
reaction can be deemed as efficient due to the percentage of yield of benzoic acid.
Conclusions:

Overall due to the percent yield calculated, 81%, it can be deemed that this reaction was a
success in the production of benzoic acid. Also the percent yield proves that the reaction that
took place was quite efficient, and through more careful techniques by the researcher, the percent
yield could be increased to be closer to that of the theoretical yield. During the experiment the
researcher noticed some crystalline substance inside of the filter flask after filtration which
contributed to the decreased percent yield of the product.
References:
Griffiths, J., Overly, K., and Broughton, S., Introductory Organic Laboratory; Techniques and
Transformations, Chem 2125, 6th Edition, 2010
Wohlrab, A. (2015) Experiment 9 prelab notes. Retrieved from:
https://blackboard.stockton.edu/webapps/blackboard/execute/content/file?
cmd=view&content_id=_796150_1&course_id=_45159_1&framesetWrapped=true