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Diastereoselective Bromination of Trans-Cinnamic Acid

The students prepared 1.4800 grams of trans-cinnamic acid using an analytical
balance and dissolved it in 8 mL of acetic acid, initially prepared by the instructor, in
a 50-mL round-bottom flask, as shown from the reflux set-up:

and was mixed by using a stirring bar under a constant temperature of 50 degrees
The students then placed a separatory funnel with 10 mL Bromine in acetic
acid above the condenser using an iron ring. Br2 in CH3COOH was added dropwise
into the round-bottom flask with a 15-minute interval until the whole amount was
completely added and light orange color persisted. After continuous stirring for 10
more minutes, still using sa stirring bar, nothing happened. Limonene was added
dropwise to the solution and a total of 6 pasteur pipettes was consumed. This
resulted to a cloudy yellow-orange solution that was further cooled to room
temperature and was placed in an ice bath and afterwards filtered using a fluted 3:1
filter paper and a receiving beaker.

Since no precipitate formed after the filtration of the yellow-orange solution,

the students added distilled water to the filtrate in the beaker that produced a
cloudy white precipitate. The original filtrate, now containing a cloudy white
precipitate, was filtered using the same 3:1 filter paper. The students then
transferred the precipitate formed from the filter paper to an Erlenmeyer flask and
dissolved it in a hot 95% ethanol. They continued to add ethanol in the flask until all
precipitate was dissolved. Afterwards, they added hot distilled water until cloudiness
appeared and an appreciable amount of hot ethanol to remove cloudiness and
obtain a clear solution. After dissolving all precipitate and, the students cooled the
solution to room temperature without any disturbances and afterwards placed it in
an ice bath for 10-15 minutes to crystallize.
The former clear solution, now with crystals, in the Erlenmeyer flask, was
filtered using a pre-weighed 3:1 filter paper and a receiving beaker. Then, the
students added cold distilled water to the clear filtrate in the beaker that produced
a cloudy white solution. The students then filtered the cloudy white filtrate using the
same pre-weighed 3:1 filter paper and the precipitate they obtained was air-dried in
the locker until the next meeting.

Organic compounds with unsaturation such as alkenes and alkynes react with
bromine (Br2) and give a positive result of decolorization of the said reagent usually
from yellow to colorless solution. In this experiment, trans-cinnamic acid, a
carboxylic acid with an unsaturation (double bond) in its second carbon and a
phenyl on its third carbon, is reacted with bromine in a nonnucleophilic solvent in
this case, acetic acid.
The reaction mechanism is called electrophilic addition of bromine to alkenes. A
cyclobromonium ion intermediate forms

+ Br2

+ Br-