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CLASSIFICATION TESTS FOR ORGANIC HALIDES Ygna Allyra M. Gamez, Imma Ericka L. Galima, Mary Lois Ara O.

Galo, Angeline Joy C. Garcia, Justine Nicolle S. Go Group 5 2A Medical Technology Organic Chemistry Laboratory ABSTRACT Understanding and classifying organic halides as organic compounds: Organic compounds contain a halogen atom bonded to a carbon atom, most are synthetic and not flammable. The objectives of this experiment was to differentiate primary, secondary and tertiary samples of organic halides based on S N reactivity and also to differentiate the SN1 and SN2, two mechanisms with organic halides. Sample compounds of chlorobenzene, n-butyl chloride, sec-butylchloride, tert-butyl chloride were analyzed with Beilstein test, alcoholic AgNO3 and NaI in acetone. Everyone of the sample compounds tested produced a positive result with the Beilstein test, in which we may aver the presence of a Chloride ion. Then had we reacted the sample with 2% ethanoic AgNO3 and put into observation SN1reactivity, all of which have attained white precipitate in divergent time except for chlorobenzene which had been observed with no reaction. On the other hand, in the SN2 phase reactivity, using NaI in Acetone, an observation was made that all had exhibited the presence of white precipitate except for sample chlorobenzene; heeded that the time required for each compound was different from what was observed in SN1. Therefore, it was inspected that there are significant differences in results delivered from the S N reactivity and that these differences may be used to classify organic halides. INTRODUCTION Organic halides are organic compounds which contain a halogen atom bonded to a carbon (C) atom. Fluorine (F), chlorine (Cl), bromine (Br), and iodine (I) are all types of halogen atoms. A compound which contains a carbon atom bonded to a fluorine atom (C-F) is called an organofluoride. On the chance the carbon atom is part of a chain of carbon atoms, the organofluoride compound is called an alkyl fluoride. If the carbon atom is contained in a benzene or phenyl ring, the organofluoride is then referred to as an arylfluoride. Other halide compounds are named in a similarly. The reactivity of organic halides depend on the halogen atom that is bonded to the carbon atom in the particular compound. Organoiodides are most reactive and can be converted into other compounds. Organobromides are less reactive compared to organoiodides but are more reactive than organochlorides. Organofluorides are the least reactive among the organic halides. Tertiary halides are known to be more reactive in an SN1 reaction than secondary halides, which are in turn more reactive than primary halides. The deviating rates of silver halide precipitation would be expected from the halogen in each of these environments, which goes as, primary < secondary < tertiary. These deviations are best determined by testing in separate test tubes genuine samples of primary, secondary, and tertiary halides with silver nitrate and observing the results. Alkyl bromides and iodides tend to react more rapidly than chlorides, and chlorides may need to be heated in order for a reaction to be observed in a reasonable period of time. Aryl halides are known to be unreactive toward the test reagent, so are any vinyl or alkynyl halides generally allylic and benzylic halides, even when primary show reactivities greater than tertiary halides because of resonance stabilization of the resulting allyl or benzyl carbocations. EXPERIMENTAL A.) Compounds Tested (or Samples Used) n-butyl chloride sec-butyl chloride tert-butyl chloride chlorobenzene 2% ethanoic AgNO3 15% NaI in anhydrous acetone

B.)Procedure 1. Beilstein Test A small loop was made on one end of the copper wire and was heated in the oxidizing zone of a non-luminous flame until the green color moved to the flame and disappeared. The loop was then cooled and dipped into the sample. The loop, later on, was heated together with the sample in the inner zone to the outer zone of anon luminous flame. A blue-green (or green) colored flame was observed to indicate the presence of chlorine, bromine or iodine. Figure 1. Beilstein Test Set Up

Figure 2. SN reactions or mechanisms 3. SN2 Reactivity: Reaction with SodiumIodide (NaI) in Anhydrous Acetone Dry tubes were used for this part of experiment. Five drops of each sample (n-butyl chloride, secbutyl chloride, tert-butylchloride and chlorobenzene) were added to two drops of 15% Sodium Iodide (NaI) in anhydrous acetone. The contents were then mixed and the group noted the time in seconds for a precipitate to form. The color of the precipitate was also observed. RESULTS AND DISCUSSION On the experiment performed, the following data was obtained: Table 1. Data Obtained Compound Used N-butyl chloride Sec-butyl chloride Tert-butyl chloride Beilstein Test Green flame Green flame Green flame Green flame

2. SN1 Reactivity: Reaction with alcoholic AgNO3

Chlorobenzene

5 drops of each sample was added (n-butyl chloride, sec-butyl chloride,tert-butyl chloride and chlorobenzene) to 20drops of 2% ethanolic AgNO3. The test tube was then shaken and the time was noted for the silver halide precipitate to form. The color of the precipitate was also observed.

The Beilstein test was performed as a beforehand test for the presence of halogens, wherein all samples was inspected with a blue-green flame, which tells us that there is a halide in the substance. Its the simplest method for confirming the presence of a halogen, but it does not positively differentiate between Chloride, Bromide and Iodide ion. The blue-green color was spotted due to the release of light from excited states of copper halide that has vaporized in the burner flame. In order to remove the traces of sodium chloride that maybe present on the wire from handling it with fingers, it was carried out by heating the copper wire before the test Table 2. Data Obtained Using SN1 Reactivity to Organic Halides Compound Used Reaction with 2% ethanolic AgNO3

N-butyl chloride

Turbid solution in 30 seconds Turbid solution in 25 seconds White precipitate formed in 20 seconds Turbid solution in 50 seconds

Tert-butyl chloride

White crystals in 15 seconds White precipitate in 15 seconds

Sec-butyl chloride

Chlorobenzene

Tert-butyl chloride

Chlorobenzene

In the test for SN1 Reactivity by reaction with alcoholic AgNO3, tert- butyl chloride was the first to produce a white precipitate followed by secbutyl chloride, n-butyl chloride lastly with chlorobenzene. The kinetics of the reaction is dependent on the alkyl halide. The more stable the carbocation intermediate the faster the rate of SN1 reaction. The solvent used should be a protic, polar solvent which would stabilize the carbocation intermediate by solvation that increases the reaction rate. This would involve inversion and retention. The SN1 reaction happens when substrate detach to a carbocation in a slow ratelimiting step, followed by a rapid attack of a nucleophile. This reaction would show first order kinetics and take place with racemization of configuration at the carbon atom.

In the test for SN2 reactivity by reaction of NaI in acetone, n-butyl chloride is the first to show a precipitate followed by sec-butyl chloride, tert- butyl chloride and chlorobenzene in 15 seconds. The kinetics of this reaction was dependent on the alkyl halide and nucleophile. Due to steric effect, the substrate effect in SN1 reaction was the opposite of SN2 reactions. It favors primary and secondary substrates. A strong nucleophile was needed for reaction to occur because it parallels basicity. The solvent should be a polar, aprotic solvent. It involves Walden inversion of configuration. The reaction occurs as the entering nucleophile attacks the halide 180 degrees away from the leaving group. The reaction exhibits second-order kinetics and it was affected by steric effect caused by the bulky group of the reagents. TheSN2 reaction favors primary and secondary substrates compared to SN2 reaction that favors tertiary substrates. REFERENCES: From book [1] Bayquen, A.V., Cruz, C.T., de Guia,R.M.,Lampa, F.F., Pena, G.T., Sarile, A.S.,Torres, P.C. (2009).Laboratory Manual in OrganicChemistry. Quezon City: C & E Publishing, Inc [2] McMurry, J. (2011). Foundations of Organic Chemistry. USA: Brooks/Cole [3] Chemical Land. Butyl Chlorides http://chemicalland21.com/industrialchem/organi c/TERT-BUTYL%20CHLORIDE.htm

Table 3. Data Obtained Using SN2 Reactivity to Organic Halides Compound Used Reaction with 15% NaI in anhydrous acetone White precipitate in 10 seconds Pale yellow precipitate in 15 seconds

N-butyl chloride

Sec-butyl chloride