Date: 4/3/2016

Name: Chris Dyga

Section #: 25,
Monday 2:30PM
Title:
Stereochemistry of Halogen Additon
Objective:
The objective of this experiment is to calculate the yield, percent yield, observed melting point
and stereochemistry of 2,3-dibromo-3-phenylpropanoic acid formed by the reaction of transcinnamic acid and bromine.
Structures and Reactions:
trans-cinnamic acid+Br2

Pyridinium Tribromide

Reagent Table:
Reagent
Acetic Acid
Trans-cinnamic Acid
Pyridinium
Tribromide

2,3-dibromo-3-phenylpropanoic acid

Acetic Acid

Mw
(g/mol)
60.05
148.15
319.82

Amount used
Fill conical vial to 1 mL after
adding other reagents
83.6 mg
202.9 mg

Safety Table:
Chemical
MSDS/First Aid

Acetic Acid

Transcinnamic
acid
Pyridinium

If inhaled-move to fresh air; eye contact-rinse

thoroughly for 15 minutes; skin contact- wash
w/soap and water; Dont induce vomitting
If inhaled-move to fresh air; eye contact-rinse
thoroughly for 15 minutes; skin contact- wash
w/warm water; Dont induce vomitting
If inhaled-move to fresh air; eye contact-rinse

Personal
Protective
Equipment (PPE)
Gloves, Goggles

Gloves, Goggles

Gloves, Goggles

Name: Chris Dyga

Section #: 25,
Monday 2:30PM
Tribromide

thoroughly for 15 minutes; skin contact- wash

w/warm water; Dont induce vomitting

Procedure:
1) 83 mg trans-cinnamic acid and 200 mg Pyridinium Tribromide were added to a 3 mL
conical vial, then acetic acid was added to fill the vial to the 1 mL mark with a Pasteur
pipet; add spin vane
2) Air condenser was connected to conical vial and apparatus was heated in pie block on
hot plate at setting of 3 for 25 minutes after the temperature of the hot plate reached
85C
3) Apparatus was removed from hot plate and 1 mL water was added to conical vial and
mixed.
4) Spin vane was removed and vial was labeled and placed in ice bath, covered with screw
cap
5) Hirsch funnel filtration system was set up by attaching rubber tubing to the flask, placing
Hirsch funnel with rubber fitting in the flask and covering the holes on the funnel with
filter paper
6) Solution was filtered and vial was rinsed with cold DI water; solid was left on filter funnel
for 10 minutes to dry, then transferred to a 3 mL conical vial w/ spin vane
7) 0.5 mL methanol was added to conical vial and vial was placed in pie block; more
methanol was added drop by drop until solution was dissolved; Water was added drop
by drop until the solution became cloudy, then heated until the solution boiled
8) Conical vial was removed from pie block and cooled to room temperature, then placed in
the ice bath for 10 minutes; During steps 7/8, Hirsch funnel was cleaned and set up
again
9) Crystals were filtered again through Hirsch funnel and vial was rinsed twice and funnel
was rinsed twice with 1 mL water; Funnel left to dry for 15 minutes
10) Recovered crystals were weighed and then placed in capillary tubes; melting point was
determined with settings given in lab
Note: Hot plate should never exceed 105C
Observations:
Pyridinium Tribromide: 202.9 mg
Trans-cinnamic acid: 83.6 mg
Acetic Acid: filled to 1 mL mark on conical vial
As apparatus with air condenser was heated, solution became orange. After being placed in the
ice bath, a white precipitate formed, which was filtered to a white crystal. As methanol was
added, the solution became clear, and as water was added, the solution became cloudy. After it
was placed in an ice bath again, another white precipitate was formed, which was filtered to a
white crystal, which is 2,3-dibromo-3-phenylpropanoic.

Name: Chris Dyga

Section #: 25,
Monday 2:30PM
Data:
The resulting product had a mass of 89.7 mg and a melting point range of 194.2-195.2C.

Analysis/Results:
1) Mechanism 1: carbocation intermediate 2 steps; 2 stereoisomers formed

Mechanism 2: bromonium ion intermediate 1 step; 2 stereoisomers formed

2) Table 1 of the lab handout gives the melting points of the possible products from the
trans-cinnamic acid reaction. The melting point range of a racemic mixture of (2R,3S)2,3-dibromo-3-phenylpropanoic acid and (2S,3R)-2,3-dibromo-3-phenylpropanoic acid is
202-204C which is very close to my observed melting point of 194.2-195.2C. These
two enantiomers of 2,3-dibromo-3-phenylpropanoic acid are therefore the products of
this reaction. Neither mechanism product is optically active because they are both a
racemic mixture of enantiomers (opposite but equal shift of polarized light); however, if
you could crystalize the product of this experiment and separate them as enantiomers,
they would shift the plane of polarized light in opposite directions but the magnitude
could be determined. This would be different than the magnitude of each enantiomer in
mechanism 1.
3) A racemic mixture of (2R,3R) and (2S,3S) would be formed by mechanism 2; but the
intermediate would be (2R,3S) or (2S,3R) instead of (2S,3S) or (2R,3R) as in trans.

Name: Chris Dyga

Section #: 25,
Monday 2:30PM
4) This reaction is stereospecific because the stereochemistry of the products is based
directly on the stereochemistry of the reactants. Stereoselectivity is when one product is
made more frequently because the mechanism to form one stereoisomer is more
favorable than the other one. In this reaction, there is no preference towards which
carbon on the intermediate the bromide ion attacks, so there can be no stereoselectivity.

Discussion:
The reaction of trans-cinnamic acid with bromine produces a racemic mixture of (2R,3S)- 2,3dibromo-3-phenylpropanoic acid and (2S,3R)-2,3-dibromo-3-phenylpropanoic acid. This was
produced following mechanism 1 and was confirmed by the melting point. The melting point of
the product was slightly below the expected melting point, and this is likely because of some
impurities that lower the melting point of the crystal. The percent yield for this experiment was
about 70%. One source of error is that when removing the crystals from the Hirsch Funnel for
massing, some of the crystals did not land on the weighing paper, and others remained on the
filter paper. Another possible source of error was that the some of the solution was not
transferred between the conical vial and the Hirsch funnel, or between the Hirsch funnel and the
conical vial. Additionally, some water may have remained on the Hirsch funnel after the 15
minutes, resulting a higher mass, but this probably had little effect, since my % yield was below
100%. There were no significant changes made to the procedure and the observations
throughout the experiment were expected and recorded above. Our table used 2 different
machines for the melting point portion of the lab to finish quicker by placing all 3 students
capillary tubes into both machines at the same time with different setting to determine that the
melting point was in the second range given in lab. Since the melting point data showed that
mechanism 2 was followed, we know that the stereochemistry of the carbon attacked by the
bromide ion in step 2 changes its stereochemistry, resulting in a molecule with R/S or S/R,
whereas the intermediate and the product of a reaction involving cis-cinnamic acid would be
R/R or S/S.