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UNIVERSITY OF SANTO TOMAS COLLEGE OF SCIENCE CHEMICAL BIOLOGY I – ORGANIC MOLECULES LAB A.Y.

UNIVERSITY OF SANTO TOMAS

COLLEGE OF SCIENCE

CHEMICAL BIOLOGY I ORGANIC MOLECULES LAB

A.Y. 2018-2019

BIOLOGY I – ORGANIC MOLECULES LAB A.Y. 2018-2019 Bromination: Stereochemistry of Bromine Addition to Trans-

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 Ac 2 O 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 cinnamic acid

148.1586 g/mol

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.

substance was taken as shown in Figure 1 and Figure 2. Figure 1. IR Spectrum of

Figure 1. IR Spectrum of Recrystallized Product

Figure 2. Figure 1. IR Spectrum of Recrystallized Product Figure 2. IR Spectrum of Cinnamic Acid

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