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J. G. Africano, C. L. Arenos, P.G. Bagazin*, A. M. Barona, M. Bautista Faculty of Pharmacy, University of Santo Tomas
Abstract Organic halides are organic compounds containing a halogen atom bonded to a carbon atom. Most organic halides are synthetic and not flammable. The objectives of this experiment were to differentiate primary, secondary, and tertiary organic halides based on SN reactivity and differentiate SN1 and SN2 mechanisms with organic halides. Sample compounds of chlorobenzene, n-butyl chloride, sec-butyl chloride, tert-butyl chloride were analyzed with Beilstein test, alcoholic AgNO3 and NaI in acetone. All samples produced a positive result with Beilstein Test. When the samples are reacted with AgNO3, tertbutyl chloride, sec-butyl chloride, n-butyl chloride produced a white precipitate in the said sequence and there is no reaction with chlorobenzene. In the test with SN2 reactivity all produced positive results with a white precipitate, n-butyl chloride first, followed by sec- butyl chloride then tert butyl chloride and chlorobenzene.
Introduction Organic halides are organic compounds in which one or more hydrogen atoms have been substituted by a halogen atom. The halogen atom can either be Chlorine, Fluorine, Bromine, or Iodine. Organic halides are considered as flame retardant and synthetic (1). If the alpha carbon atom is sp3 hybridized in the compound, the organic halide can be classified as primary, secondary or tertiary that is dependent on the degree of substitution of alpha hydrogen atom by an R group (2). Organic halides are can be classified depending on the halogen atom position on the chain of carbon atoms. The carbon which is attached with the halogen atom is linked up with only one other alkyl group in primary halogenoalkanes, whereas directly linked up with two and three other alkyl groups in secondary halogenoalkanes and tertiary halogenoalkanes respectively (3).
Procedure. A small loop was made with one end of the copper wire and heated on a non-luminous flame until the green color disappears. It was cooled then dip into the sample. A blue-green or green colored flame indicates the presence of chlorine, bromine, or iodine. B. SN1 Reactivity: Reaction with Alcoholic AgNO3 Procedure. 5 drops of the sample were added to 20 drops of 2% ethanolic AgNO3. The mixture was shaken and the time before the precipitate forms and color were recorded. SN2 Reactivity: Reaction with NaI in Acetone Procedure. 5 drops of the sample were added to 2 drops of 15% NaI in anhydrous acetone. It was mixed and the time before the precipitate forms and color were recorded.
C. tert- butyl chloride chlorobenzene
By the use of substitution reaction with a nucleophile, the reaction of an electron pair donor (the nucleophile, Nu) with an electron pair (the electrophile). An sp3-hybridized electrophile must have a leaving group (X) in order for the reaction to take place (4). The reaction is SN1 or unimolecular if the rate of reaction is dependent on the organic halide and it is SN2 or bimolecular if the rate of reaction is dependent on both the organic halide and the nucleophile (2)The following tests were performed: Beilstein test is a simple chemical test used in chemistry as a qualitative test for halides. It was developed by Friedrich Konrad Beilstein.(5) To test for SN1 reactivity the samples were reacted with alcoholic AgNO3 and to test for SN2 reactivity it is reacted with NaI in acetone(2). In this experiment the group should be able to attain the following: differentiate primary, secondary, and tertiary organic halides based on SN reactivity and differentiate SN1 and SN2 mechanisms with organic halides. Methodology
Results Results obtained from experiment were tabulated (see table 1) Sample n-butyl chloride Sec-butyl chloride Tert- butyl chloride Chlorobenzene Color of Flame Blue-green flame Blue- green flame Blue-green flame Green flame
Table 1. Reactions of Samples in Beilstein Test
A. Beilstein Test : Copper Halide Test
the substrate effect in SN 1 reaction is the opposite in SN 2 reactions.T. 2003 Bayquen. This reaction shows first order kinetics and take place with racemization of configuration at the carbon atom. It involves Walden inversion of configuration.butyl chloride and we did classification tests for these organic halides. polar solvent that stabilizes the carbocation intermediate by solvation that increases the reaction rate. The solvent should be a polar.butyl chloride was the first to produce a white precipitate followed by sec-butyl chloride. C. A. (2009). a textbook (2) of Organic Chemistry.This is a test for the presence of halide by the presence of a blue-green colored flame. The blue-green color is due to the emission of light from excited states of copper halide that has vaporized in the burner flame.com/industrialchem/organi c/n-BUTYL%20CHLORIDE. . In terms of stereochemistry. Inc.. Reactions of Samples with NaI Discussion Order of appearance of ppt 1 (3 seconds) 2 (7 seconds) 3 (11 seconds) 4 (20 seconds) in Acetone (5) In the experiment. USA: New Age International.butyl chloride and chlorobenzene. The more stable the carbocation intermediate the faster the rate of SN 1 reaction.organicchemistry.Precipitate n-butyl chloride sec-butyl chloride tert. The kinetics of the reaction is dependent on the alkyl halide. G. Reactions of Samples with alcoholic AgNO3 sample n-butyl chloride Sec-butyl chloride Tert. F.M. The SN 2 reaction favors primary and secondary substrates compared to SN 1 reaction that favors tertiary substrates. and Raj Bansal. The first test was the Beilstein Test. The kinetics of this reaction is dependent on th alkyl halide and nucleophile.butyl chloride Chlorobenzene No precipitate formed White Precipitate White Precipitate White Precipitate Table 3. A strong nucleophile is needed for reaction to occur because it parallels basicity. Br and I. sec-butyl chloride. Reactions involved: Cu + O2 RX + CuO CuO (black solid) CuX2+ CO2+H2O In the test for SN1 Reactivity by reaction with alcoholic AgNO3 tert. The solvent used should be a protic.. indicating that all samples contain halides but this test is not enough to differentiate between Cl. In the test for SN 2 reactivity by reaction of NaI in acetone.org/wiki/Beilstein_test (3) (4) Table 2. aprotic solvent.Lampa. The CuX2 imparts the blue. A.shtm http://en. The reaction exhibits second-order kinetics and it is affected by steric effect caused by the bulky group of the reagents.. All samples produced a green or blue green colored flame. The reaction occurs as the entering nucleophile attacks the halide 180 away from the leaving group.V. P. It favors primary and secondary substrates. R.butyl chloride chlorobenzene White precipitate White precipitate White Precipitate No reaction appearance of precipitate 3 (10 seconds) 2 (8 seconds) 1 (3 seconds) 4 (striations appeared during first drop) Sources: (1) Bernthsen. tert. Sarile.green flame.S. http://chemicalland21. In terms of stereochemistry. Pena.. followed by a rapid attack of a nucleophile. de Guia. Due to steric effect.. A good leaving group is important for the reaction to occur. tert. n-butyl chloride is the first to show a white precipitate followed by sec-butyl chloride.htm http://www. Cruz.F.C.wikipedia. August .org/namedreactions/nucleophilicsubstitution-sn1-sn2. n-butyl chloride and no reaction with chlorobenzene.T. this involves inversion and retention. Torres. Quezon City: C & E Publishing. we were given samples of nbutyl chloride. The SN 1 reaction happens when substrate dissociate to a carbocation in a slow rate-limiting step.Laboratory Manual in Organic Chemistry..
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