UNIVERSITY OF SANTO TOMAS

COLLEGE OF SCIENCE
CHEMICAL BIOLOGY I – ORGANIC MOLECULES LAB
A.Y. 2018-2019

Bromination: Stereochemistry of Bromine Addition to Trans- Cinnamic Acid

Matthew Aquino, Juan Kristofer Aranilla, Dianne Coleen Baylosis, and John David Brosola

ABSTRACT
The purpose of this experiment was to explore the addition of bromine to trans-cinnamic acid
and identify the product based on its melting point. The bromination of trans-cinnamic acid was
completed to determine dibromide’s stereochemical structure and its mechanism. After the
addition of bromine to trans-cinnamic acid, the product was identified by its infrared spectrum
resulting in erythro-2,3-Dibromo-3-phenylpropanoic acid after comparing similar properties.This
experiment carried out the addition of trans-cinnamic acid to bromine to produce 2,3-dibromo-3-
phenylpropanoic acid. Reactivity of the double bond in cinnamic acid is assessed by the said
addition of bromine.

INTRODUCTION
2,3-dibromo-3-phenylpropanoic acid was synthesized from the reaction of trans-cinnamic acid
and bromine. Bromination is an any reaction or process in which bromine, and no other
elements, are introduced into a molecule. Cinnamic acid was used because it is a naturally
occurring compound. Cinnamic acid exists as trans and cis isomers, but the trans form is the
one most often found in nature and is the article of commerce. It is obtained from cinnamon bark
and balsam resins such as storax. It was first isolated in 1872 by F. Beilstein (of Handbook of
Organic Chemistry fame) and A. Kuhlberg. It is synthesized by the Perkin reaction between
Ac2O and PhCHO. trans-Cinnamic acid is used in the manufacture of flavors, dyes, and
pharmaceuticals; but its major use is for the production of its methyl, ethyl, and benzyl esters.
These esters are important components of perfumes. The acid is also a precursor to the
sweetener aspartame.
The bromination of trans-cinnamic acid was completed to determine dibromide’s stereochemical
structure, and from there, we determined whether the reaction is carried out by the usual
bromonium ion mechanism or a different mechanism.This is an important aspect in the
determination of dibromide’s stereochemical structure, as a mechanism can be affected by
changing a reactants structure. After the addition of bromine to trans-cinnamic acid, the product
is identified by its melting point and infrared spectrum. The product could be erythro-dibromo,
threo-dibromo, or a combination of both. Although obtaining a product consisting of both erythro
and threo is possible, it results in an impure substance with a broad melting point range that
contrasts pure dibromide. These particular compounds of erythro and threo are named as such
to distinguish their two chiral centers, but no plane of symmetry.
 RESULTS AND DISCUSSION
The experiment carried out the addition of trans-cinnamic acid to bromine to produce 2,3-
dibromo-3-phenylpropanoic acid. Reactivity of the double bond in cinnamic acid is assessed by
the said addition of bromine. Initial weights of the materials for reflux set up were recorded as
shown in Table 1.

Materials Weight
Trans Cinnamic Acid 0.6 g
Empty Beaker 28.64 g
Crude + Beaker 29.199 g
Crude 0.559 g
Filter Paper 0.162 g

Table 1. Weights of Materials used in Reflux Set Up

The mixing of trans-cinnamic acid with 10% bromine in dichloromethane over a low heat
allowed for an elevated speed of the reaction. The mixture was cooled to room temperature and
was placed in a water bath. It was then cooled to crystallization and vacuum filtered to allowed
for the separation of 2,3-dibromo-3-phenylpropanoic acid. The final recrystallized product was
weighed in to be .2808 g while the initial crude weight was 0.559 g. Theoretical weight as well
as percent yield was then calculated utilizing the data presented in Table 2.

Data Value
Molecular weight 148.1586 g/mol
cinnamic acid
Molecular weight product 307.969 g/mol
Mole cinnamic acid 0.00405 moles
Mole product 0.00911 moles
Mole ratio 4.45058 moles

Table 2. Data Table

Theoretical weight of the product was obtained using the following equation:
 Moreover, the percent yield recorded was 10 using the following calculation:

IR spectrum of both cinnamic acid and the recrystallized substance was taken as
shown in Figure 1 and Figure 2.

Figure 1. IR Spectrum of Recrystallized Product

Figure 2. IR Spectrum of Cinnamic Acid

IR spectrum of recrystallized substance shows the presence of aromatic rings around

1600 as well as C-H stretch around 2850. Melting points of recrystallized product labeled as
substance A and cinnamic acid labeled as substance B were recorded as shown in Table 3.
With the recrystallized product having higher melting points comparing to the cinnamic acid
 A B
(Recrystallized) (Cinnamic Acid)
T1 132.6°C 128.9°C
(Substance starts
to melt)
T2 135.8°C 132.4°C
(Substance
completely
melted)
Table 3. Melting points
References:
Experiment is a modified version of an experiment found in: Lehman, J.W. Operational Organic
Chemistry: a problem-solving approach to the laboratory course, 3rd ed., Prentice-Hall, Upper
Saddle River, New Jersey, 1999.
Illustrated Glossary of Organic Chemistry. (n.d.). Retrieved from
http://www.chem.ucla.edu/~harding/IGOC/B/bromination.html
Sneller, J., & Sneller, J. (2015, November). Bromine Addition to Trans-Cinnamic Acid. Retrieved
from https://www.academia.edu/22866433/Bromine_Addition_to_Trans-Cinnamic_Acid
Stockton University, Stereochemistry of Bromine Addition to Trans-Cinnamic Acid -
Stereochemistry of Bromine Addition to Trans-Cinnamic Acid Abstract. Retrieved from
https://www.coursehero.com/file/8741919/Stereochemistry-of-Bromine-Addition-to-Trans-
Cinnamic-Acid/
Trans-Cinnamic acid. (n.d.). Retrieved from https://www.acs.org/content/acs/en/molecule-of-the-
week/archive/c/trans-cinnamicacid.html