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CHM143L Organic Chemistry 2 Laboratory 3 rd Quarter SY 2014-2015

Factors Affecting the Relative Rates of Electrophilic Aromatic Substitution Reactions

Tagalog, Christian, Tolentino, Aika Cecille, I. Terrado, Rence, Valencia, Ifame

Prof. Oliver, School of Chemical Engineering, Mapua Institute of Technology; Aika Tolentino, CHM143L/A31, School of Chemical Engineering and Chemistry, Chemical Engineering, Mapua Institute of Technology

ABSTRACT

The experiment named Melting Point and Boiling Point of Organic Compounds aims to show the factors that affects the physical properties of Organic Compounds such as the Boiling point and the Melting point. Certain techniques are used to further help the people who conducts the experiment to achieve more accurate and précised results. In this paper contains certain information on boiling point and melting point and what affects them to change. The methods done are also used in other fields to determine the boiling point and melting point of the compound. The group was assigned to determine the range of the boiling point and the melting point and to compare their work to the true value of the physical property constant. Some ranges are not in the scope of the true value because of impurities of apparatus and also due to improper focus on the experiment therefore conducting minimal errors. Brief discussions and explanations were gathered for more understanding of this experiment.

Keywords: Boiling point, Melting point, Organic Compounds, Intermolecular forces, Impurity, Branching

INTRODUCTION

Electrophilic aromatic substitution is an organic reaction in which an electrophile replaces an atom attached to an aromatic system. Some of the most important electrophilic aromatic substitutions are aromatic nitration, aromatic halogenation, aromatic sulfonation, and acylation and alkylating Friedel-Crafts reactions. However, in this experiment, only aromatic halogenation was shown. Here, phenol, chlorobenzene, p-nitrophenol, aspirin, benzene, anisole and acetanilide will undergo bromination reactions and the products from these reactions will be isolated, purified and analysed. Here, the substituted benzenes react differently in depending on the nature of the substituent attached to the compound. The substituent could make the ring more reactive than benzene if it functions as an activator. If not, it makes the ring less reactive than benzene. Substituents are also classified according to their orientations. They are classified as ortho-para if they function as activators and meta if it functions as deactivator. Aside from the nature of the substituent, other factors like temperature and solvent affect the rate of reactions. The purposes of this experiment are: to visualise the effect of substituents in the relative rates of electrophilic aromatic substitution, to know the effect of solvent on the reaction rates, and to know the effect of temperature on the rates of reaction.

MATERIALS AND METHODS

A proper

attire was strictly followed

to

minimize the

impact

of

accidents

that

might

occur

during

the

experiments. Especially, protective goggles and mask

was worn to avoid injury.

The reagents used for this experiment were 0.2M solution in ethyl acetate of benzene, chlorobenzene, aspirin, acetanilide, p-nitrophenol, anisole; a bromine solution; a 0.05 bromine in cyclohexane, and bromine in acetic acid. As for apparatus, micro test tubes with cork stopper, hot water bath, dropper, hot plate, test tube rack, and thermometer were used. These apparatus were cleaned before performing the experiment to avoid possible source of error in the process.

For the first part of the experiment, a 0.2M solutions in ethyl acetate of benzene, chlorobenzene, aspirin, acetanilide, p-nitrophenol, anisole and phenol are the organic compounds mix properly. It was occasionally observed for any evident reaction.

that were tested for any substituent effect. Twenty drops of each solution was transferred in separated test tubes.

 
CHM143L Organic Chemistry 2 Laboratory 3 Quarter SY 2014-2015

CHM143L Organic Chemistry 2 Laboratory 3 rd Quarter SY 2014-2015

 

Then twenty drops of bromine solution was added to each test tubes. The time of addition was noted and the

 

COMPOUND

REACTIONS INVOLVED

 

time of reaction was recorded. The test tubes were shaken to have the solutions to As for the second part of this experiment which is the solvent effect, 0.2M solutions

Benzene

time of reaction was recorded. The test tubes were shaken to have the solutions to As
 

in ethyl acetate of anisole was tested. A twenty drops of anisole solution was transferred in a test tube and a 20

Chlorobenzene

drops of freshly prepared 0.05M bromine in cyclohexane

Aspirin

was added to it. Then on another test tube, 20 drops of anisole solution and 20 drops of bromine in acetic acid

Acetanilide

was transferred on the test tube. The reactivity of the anisole solution in two solvents were compared.

P-nitrophenol

Anisole

Lastly, as for the third part of this experiment which is the

preheating a 400mL beaker containing 300mL of water.

Phenol

temperature effect, a 0.2M acetanilide in ethyl acetate was tested. A 20 drops of 0.2M acetanilide in ethyl

II.

Solvent Effect

acetate was transferred in three different test tubes and another 20 drops of bromine in acetic acid was added to it each test tubes. The test tubes were heated in 50°C,

Table 2.1. (Time of Decolorization of Solvent Effect)

 

COMPOUND

 

TIME OF

REMARKS

 

70°C and 90°C respectively in water bath prepared by

DECOLORIZATION

 

The time of decolorization was observed.

Anisole +

23 minutes ( turned

Cloudy upon

 
 

Bromine in

pale yellow)

addition of

 

RESULTS and DISCUSSIONS

 

cyclohexane

30 minutes (turned

cyclohexane

  • I. Substituent Effect

clear)

 
 

Anisole +

55

minutes

Slower reaction

 
 

Table 1.1 (Time of Decolorization of Substituent Effect)

 

Bromine in

   

acetic acid

 

COMPOUND

TIME OF

REMARKS

 

DECOLORIZATION

III.

Temperature Effect

 
 

Benzene

 

Dark red

 
 

Chlorobenzene

 

Dark red

Table 3.1. (Time of Decolorization of Solvent Effect)

 

COMPOUND

 

TIME OF

REMARKS

 
 

Aspirin

17 minutes

Dark red (but

 

lighter than

 

DECOLORIZATION

 
   

benzene and

90°C

52 seconds

Turned pale

 

chlorobenzene)

 

yellow

 

Acetanilide

1 second

orange

70°C

71

seconds

Turned pale

 
 

P-nitrophenol

3 minutes

Dark orange

   

yellow

 

50°C

90

seconds

Turned pale

 
 

Anisole

8 minutes

Light orange

 
     

yellow

 

Phenol

19 minutes

orange

 
   

Table 1.2 (Reaction involved)

Graph 1.1 (Temperature Effect)

CHM143L Organic Chemistry 2 Laboratory 3 rd Quarter SY 2014-2015
CHM143L Organic Chemistry 2 Laboratory
3 rd Quarter SY 2014-2015

CONCLUSIONS AND RECOMMENDATIONS

REFERENCES

1. Klein, D. (2012) Organic Chemistry. John Wiley &Sons, Inc. NY, America.

2. Cruz, K. and Miranda M. Oragnic Laboratory

Manual,