CLASSIFICATION TESTS FOR HYDFROCARBONS Group 9

RAMOS, Sharina Joy; REYES Aina Marie; REYES Jallisa Maan; RUBIO, John Michael; SABINO Patricia Anne; SANTOS, Carlos Rafael

ABSTRACT
The experiment was performed in order to differentiate primary, secondary, and tertiary organic halides based on their SN reactivity; and also to differentiate SN1 and SN2 mechanism with organic halides.[1] The four sample compounds to be tested are n-butyl chloride, sec-butyl chloride, tert-butyl chloride and chlorobenzene. Three tests are to be conducted for these compounds to react namely: Beilstein Test (Copper Halide Test); SN1 Reactivity (Reaction with Alcoholic AgNO3); and SN2 Reactivity (Reaction with NaI in Acetone). The four compounds reacted in the Beilstein test with a green flame which indicates the presence of chlorine in each compounds. The next test, S N1 Reactivity allowed the compounds to react with 2% ethanolic AgNO3 which gives n-butyl chloride and chlorobenzene no precipitate while sec-butyl chloride and tert-butyl chloride yielded a white precipitate. The last test performed was the SN2 Reactivity. This test used 15% NaI anhydrous acetone to yield a white precipitate in all of the compounds.

INTRODUCTION
Organic halides are mostly synthetic and non-flammable in nature. They are compounds that contain a halogen atom bonded to a Carbon atom. This experiment was conducted to differentiate primary, secondary, and tertiary organic halides based on their SN reactivity; and also to differentiate SN1 and SN2 mechanism with organic halides. Depending on the degree of the - hydrogen atom by an R group, if the -carbon atom is tetragonal and sp3 hybridized the organic halide may be classified as primary, secondary and tertiary.[1] The Beilstein test or also known as Copper Halide Test is a simple chemical qualitative test for halides developed by Friedrich Beilstein. It was used to determine the presence of halogen in the compound. For this experiment the presence of chloride was observed through the appearance of a green flame. The SN1 and SN2 mechanism were differentiated because the two are unimolecular and bimolecular respectively. The SN1 mechanism is a two-step mechanism wherein the rate-determining step depends solely in the haloalkane in the compound.[6] SN1 mechanism prefers neutral or acidic medium and this mostly reacts with tertiary organic halides. The SN2 mechanism as what is mentioned earlier is a bimolecular reaction because it is not only the haloalkane which contributes to the rate-determining step but also the nucleophile present in the mechanism.[7] This mechanism happens

simultaneously which makes it a one-step reaction mechanism. The SN2 mechanism prefers a basic medium because it strengthens the nucleophilic reagent and is also very effective to mostly primary organic halides.

EXPERIMENTAL A.Compounds Tested

1. N-butyl chloride

Figure1. Condensed structural formula of Nbutyl chloride. 2. Sec-butyl chloride

Figure2. Condensed structural formula of secbutyl chloride. 3. Tert-butyl chloride

formed. The time before the precipitate formed was noted. And the color of the precipitate was described. Note: The solution of the reagent should not be turbid when used. 3. SN2 Reactivity: Reaction with NaI Acetone A clean and dry test tube was used in this procedure for the experiment to be error free. 5 drops of sample was mixed with 2 drops of 15% NaI in anhydrous acetone. It was mixed thoroughly. The time before the precipitate was formed was noted. And the color of the precipitate was described. Note: The solution of the reagent should not be turbid when used.

Figure3. Condensed structural formula of tertbutyl chloride. 4. Chlorobenzene

RESULTS AND DISCUSSION

The Beilstein test yielded a positive result because all the compounds tested were able to react with the non-luminous flame. This indicated the presence of a halogen, more specifically, in this experiment was chloride.

Figure4.

Condensed chlorobenzene.

structural

formula

of

Compounds Used N- butyl chloride Sec-butyl chloride Tert- butyl chloride Chlorobenzene

Beilstein test Green flame Green flame Green flame Green flame

Table1. Results of Beilstein or Copper halide

test.

B.Procedure
1. Beilstein Test: Copper Halide Test A copper wire and a Bunsen burner is needed in this procedure. A small loop was formed with the copper wire and it was thoroughly heated in the oxidizing zone of a nonluminous flame. It was continuously heated until the green color imparted to the flame disappeared. The loop of the heated copper wire was cooled down for a while and then dipped into the sample that is to be tested. The loop was heated with the sample in a non-luminous flame, firstly in the inner zone and then to the outer zone near the edge of the flame. A green color was exhibited by the flame and it was due to the presence of chloride. 2. SN1 Reactivity: Reaction AgNO3 5 drops of sample was drops of 2% ethanolic AgNO3. thoroughly until a silver halide with Alcohol mixed with 20 It was mixed precipitate was

Figure5. Green-flame exhibited by the beilstein test or also known as copper halide test. In the test of SN1 Reactivity: Reaction with Alcohol AgNO3, the reaction of the sample was observed and the time consumed before it was precipitated was noted. The samples reacted

with 2% ethanolic AgNO3 which gives n-butyl chloride and chlorobenzene no precipitate while sec-butyl chloride and tert-butyl chloride yielded a white precipitate.

Compounds Used N- butyl chloride Sec-butyl chloride Tert- butyl chloride Chlorobenzene

Beilstein test No precipitate White Precipitate, slow reaction White Precipitate, immediate reaction No precipitate

[4]http://www.chemicalforums.com/index.php?to pic=29811.0 [5]http://www.mhhe.com/physsci/chemistry/care y5e/Ch08/ch8-2.html [6]http://facultystaff.vwc.edu/~jeaster/courseinf o/Tutorials/reactions/Sn1.htm [7]http://facultystaff.vwc.edu/~jeaster/courseinf o/Tutorials/reactions/Sn2.htm [8]http://ull.chemistry.uakron.edu/organic_lab/b eil/ [9]http://en.wikipedia.org/wiki/Halocarbon

Table2. Results of SN1 Reactivity: Reaction with

Alcohol AgNO3. The test for SN2 Reactivity: Reaction with NaI Acetone, yielded a white precipitate in all the compounds however, some differ in their rates. N-butyl reacted immediately, while the other compounds reacted 1-2 seconds after the mixing of the sample and the 15% NaI in anhydrous acetone.

Compounds Used N- butyl chloride Sec-butyl chloride Tert- butyl chloride Chlorobenzene

Beilstein test White Precipitate, immediate reaction White Precipitate, slow reaction White Precipitate, slow reaction White Precipitate, slow reaction

Table3. Results of SN2 Reactivity: Reaction with

NaI Acetone.

REFERENCES Books:
[1] Bayquen, A.V., Cruz, C.T., de Guia, R.M., Lampa, F.F., Pena, G.T., Sarile, A.S., and Torres, P.C. (2009) Organic Chemistry. 839 EDSA, South Triangle, Quezon City: C & E Publishing, Inc. Internet Sources: [2]http://sydney.edu.au/science/chemistry/~geo rge/halides.html [3]http://www.masterorganicchemistry.com/201 2/08/08/comparing-the-sn1-and-sn2-reactions/