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CLASSIFICATION TESTS FOR PRIMARY, SECONDARY AND TERTIARY ORGANIC HALIDES BASED ON THEIR SN REACTIVITY

Serrona, M.R.A., Soriano, M.C., *Tolentino, S.C., Vicencio, N., Yu, B.N. 2D, Faculty of Pharmacy, UST

Abstract This experiment was conducted to differentiate primary, secondary and tertiary organic halides based on their SN reactivity and differentiate SN1 and SN2 mechanisms with organic halides. The samples used were n-butyl chloride, sec-butyl chloride, tert-butyl chloride and chlorobenzene. For detecting the presence of halides in the sample, the Beilstein test or the copper halide test was conducted. And as a result, all the samples produced green flame upon heating the copper wire which contains the samples. In determining the Sn1 reactivity of the samples, the samples are made to react with 2% ethanolic silver nitrate. As observed, all the samples have produced a white precipitate except for cholorbenzene because chlorobenzene is already stabilized by resonance. Among all the samples that produced precipitate with the addition of the 2% ethanolic silver nitrate, tert-butyl chloride is the fastest while n-butyl chloride is the slowest showing that during SN1 reactions, tert-butyl chloride has the highest reactivity. In determining the SN2 reactivity of the samples, the samples are made to react with 15% sodium iodide in anhydrous acetone. As a result, all the samples produced white precipitate except for cholorobenzene. Among all the samples that produced precipitate with the addition of the 15% sodium iodide in anhydrous acetone, n-butyl chloride is the fastest and tert-butyl chloride is the slowest showing that n-butyl chloride has the highest reactivity in SN2 reaction. The samples used were n-butyl bromide, sec-butyl bromide, tert-butyl bromide and chlorobenzene as showed in figure 1. For the Beilstein test, a copper wire was used. The one end of the copper wire was made to a small loop and was heated directly in the oxidizing zone of a nonluminous flame. It was continuously heated until the green color imparted to the flame has disappeared. Cool the loop slightly and dip it into one of the samples. Heat the loop with the sample in a non-luminous flame. For the SN1 reactivity, the samples were reacted with ethanolic silver nitrate. In a test tube, add 5 drops of the sample to 20 drops of 2% ethanolic silver nitrate. Shake and record the time for a silver halide precipitate to form. Note: the solution of the reagent should not be turbid when used to prevent contamination as it will affect the

Introduction: Unlike other organic compounds, most organic halides are synthetic. Organic halides are not flammable. If the alphacarbon atom is tetragonal or sp3 hybridized compound, the organic halide may be classified as primary, secondary or tertiary, depending on the degree of substitution of the alpha-hydrogen atom by an R group. (Bayquen, et al., 2009) The objectives of this experiment are to differentiate primary, secondary and tertiary organic halides based on their SN reactivity and differentiate SN1 and SN2 mechanisms with organic halides.

Materials and Methods:

result of the experiment. This procedure was done to all of the samples. For the SN2 reactivity, the samples were reacted with sodium iodide in acetone. Dry test tubes were used for this. Add 5 drops of the sample to 20 drops of 15% sodium iodide in anhydrous acetone. Mix the contents and not the time required for precipitate to form.

As seen in both Table 2 and Table 3, only chlorobenzene has not produced precipitate. This is because chlorobenzene is already stabilized by resonance.

Table 1: Data collected when the samples undergone Beilstein test Compound used n-butyl chloride Sec-butyl chloride Tert-butyl chloride Chlorobenzene Beilstein test Green flames Green flames Green flames Green flames

Table 2: Time recorded when the samples reacted with 2% ethanolic silver nitrate to produce precipitate Compound used Reaction with 2% ethanolic silver nitrate 4 minutes and 25 seconds 1 minute and 17 seconds 1 second No precipitate produced

Figure 1: Samples used for this experiment

n-butyl chloride Sec-butyl chloride

Results and Discussion: Tert-butyl chloride As showed in Table 1 all the samples produced green flames in Beilstein test therefore confirming that all the samples were organic halides. The time recorded in Table 2 for the SN1 reactivity shows that tert-butyl chloride reacts the fastest with 2% ethanolic silver nitrate while n-butyl chloride reacted the slowest thus showing tert-butyl chloride has the highest reactivity during Sn1 reactions. In SN1 reactivity, tert-butyl chloride is the fastest to react therefore it has the highest reactivity. But it is opposite in SN2 reactions. As showed in Table 3, n-butyl chloride has the fastest time compared to the others and tert-butyl chloride is the slowest. This shows that n-butyl chloride has the highest reactivity in the SN2 reaction. Chlorobenzene

Table 3: Time recorded when the samples reacted with 15% sodium iodide in anhydrous acetone to produce precipitate Compound used Reaction with 15% sodium iodide in anhydrous acetone 1 second 2 second 3 second No precipitate produced

n-butyl chloride Sec-butyl chloride Tert-butyl chloride Chlorobenzene

References: Bayquen, A., Cruz, C., Guia, R., Lampa, F., Pena, G., Sarile, A., & Torres, P. (2009). Laboratory Manual in Organic Chemistry. Quwzon City, Philippines: C&E Publiching Inc. Klein, D. R. (2012). Organic Chemistry. Hoboken, N. J. : Wiley. MucMurry, J. (2012). Organic Chemistry. Belmont, CA: Cole, Cengage Learning. Smith, J. (2011). Organic Chemistry. New York: McGraw Hill. Solomons, T. W. (2011). Organic Chemistry. Hoboken, N. J.: Wiley. Straumanis, A. (2012). Organic Chemistry: a guided inquiry. Boston, MA: Houghton Muffin.

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