CLASSIFICATION TESTS FOR ORGANIC HALIDES

Jesse Lance Jariel, Hannah Lorraine Lim, Johnvee B. Magana, Liezel Mamburam and Karla Matienzo Group 5 2C Pharmacy Organic Chemistry Laboratory

ABSTRACT
In the experiment Organic halides such as n-butyl chloride, sec-butyl chloride, tert-butyl chloride and chlorobenzene were subjected to Beilstein test and another test using reagents of Ethanolic Silver Nitrate and Sodium Iodide in anhydrous acetone; the experiment is to differentiate and know the SN1 and SN2 reactivity of these organic halides. Unlike other organic compounds, most organic halides are synthetic and non-flammable; they are also classified as primary, secondary or tertiary depending on degree of substitiution. A Beilsten test was performed that imparted a green flame on every sample and the use of 5 drops of each of the sample and few drops of the reagents, different reactions were seen. In Ethanolic Silver Nitrate all except chlorobenzene produced a white precipitate; same with reactions of the sample in Sodium Iodide all except chlorobenzene produced a precipitate.

INTRODUCTION
Organic halides are compounds that contain one or more halogen atoms in addition to carbon and hydrogen are called organic halides.[1] The reactivity of organic halides depends on the halogen atom that is bonded to the carbon atom in the particular compound and 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. [2] An organic halide can be named as primary, secondary and tertiary depending on the degree of substitution of the alpha hydrogen atom by an R group on an sp3 hybridized alpha carbon atom.[3]The reactivity of organic halides can be differentiated via a substitution reaction with a nucleophile, depending on which reactant molecule is involved in the rate-determining step, it is unimolecular (SN1) if the rate of reaction depends on the organic halide and bimolecular (SN2) if it is dependent on both the organic halide and nucleophile. The purpose of the experiment is to (1) Differentiate primary, secondary and tertiary organic halides based on their SN reactivity and (2) Differentiate SN1 and SN2 mechanisms with organic halides

B.Procedure 1. Beilstein Test: Copper Halide Test A small loop was made at one end of the copper wire and was heated in the oxidizing zone of a non luminous flame until a green flame imparted, it was then cooled and dip on the sample and heated once more that imparted a blue green or green flame. 2.SN1 Reactivity: Reaction with Alcoholic Silver Nitrate 5 drops of the sample was added to 20 drops of 2% Ethanolic Silver Nitrate, the sample was shaked and the precipitate form where the color and time in seconds and minutes for it were recorded and observed 3.SN2 Reactivity: Reaction with Sodium Iodide in Acetone Figure2. SN2 Reactions With the use of dry test tubes 5 drops of the sample was added to 2 drops of 15% Sodium Iodide in anhydrous acetone, the sample was mixed and the color and time required for the precipitate to form was recorded.

RESULTS AND DISCUSSION

On the experiment performed results were obtained. Compound used Beilstein Test n- butyl chloride Sec-butyl chloride Tert-butyl chloride Chlorobenzene Table1. Beilstein Test Green flame Green flame Green flame Green flame

EXPERIMENTAL
A.Sample used n-butyl chloride sec-butyl chloride tert-butyl chloride chlorobenzene 2% ethanoic AgNO3 15% NaI in anhydrous acetone

Copper wire Green flame

after the rate-limiting dissociation has occurred; thus cannot affect the reaction rate. The solvent must be a polar, aprotic solvent because it stabilizes the carbocation intermediate by salvation,thereby increasing the reaction rate. In the experiment all the samples formed white precipitate except for chlorobenzene. H2O > 80% Ethanol > 40% Ethanol > Ethanol Compound used n- butyl chloride Sec-butyl chloride 15% Sodium Iodide White precipitate White precipitate, yellow solution White precipitate No precipitate

Figure1. Beilstein test The Beilstein test is a simple chemical test used in chemistry as a qualitative test for halides, the blue-green or green color is a result due to the excited states of copper halide that vaporizes in the Bunsen burner. RX + CuO CuX2 + CO2 + H2O CuX2 is volatile; imparts in blue-green flame Compound used n- butyl chloride Sec-butyl chloride Tert-butyl chloride Chlorobenzene Ethanolic Silver Nitrate White precipitate White precipitate White precipitate No precipitate Tert-butyl chloride chlorobenzene

Table3. SN2 Reaction and Results

Chlorobenzene

n- butyl chloride

secbutyl chloride

tertbutyl chloride

Figure2. SN2 Reactions SN2 reaction (also known as bimolecular nucleophilic substitution) is a type of nucleophilic substitution, where a lone pair from a nucleophile attacks an electron deficient electrophilic center and bonds to a leaving group. In the test for SN2 reactivity by reaction of NaI in acetone, n-butyl chloride is the first to show a white precipitate followed by sec-butyl chloride, tert- butylchloride and chlorobenzene with no precipitate. The kinetics of this reaction is dependent on the alkyl halide and nucleophile. Due to steric effect, the substrate effect in SN1 reaction is the opposite in SN2 reactions. It favors primary and secondary substrates. A

Table2. SN1 Reactions and results Organic halides can be differentiated with the reaction to alcoholic AgNO3 for the SN1 reactivity of organic halides such as substitution reaction. The substrate effect emphasizes that the more stable the carbocation intermediate, the faster the SN1 reaction. 3> 2> 1> -CH3 reaction rate =k [RX] A good leaving group is needed in a reaction The nucleophile in an SN1 reaction is hardly affected. It does not enter into the reaction until

strong nucleophile is needed for reaction to occur because it parallels basicity. The solvent should be a polar, aprotic solvent. In terms of stereochemistry, It involves Walden inversion of configuration. The reaction occurs as the entering nucleophile attacks the halide 180away from the leaving group. The reaction exhibits second-order kinetics and it is affected by steric effect caused by the bulky group of the reagents. The SN2 reaction favors primary and secondary substrates compared to SN1 reaction that favors tertiary substrates.

REFERENCES:
[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 Organic Chemistry. Quezon City: C & E Publishing, Inc. [2] Organic Chemistry Portal.Nucleophilic Substitution. http://www.organicchemistry.org/namedreaction s/nucleophilic-substitution-sn1-sn2.shtm 9/12/11 [3] Chemical Land.Butyl Chlorides http://chemicalland21.com/industrialchem/organi c/TERT-BUTYL%20CHLORIDE.htm 9/12/11 Scribd.com [4]http://www.scribd.com/doc/38392039/Classifi cation-Tests-for-Organic-HalidesFINAL Sciencejrank.org [5]http://science.jrank.org/pages/3192/HalideOrganic Wikepedia.org http://en.wikipedia.org/wiki/SN2_reaction