CLASSIFICATION TESTS FOR ORGANIC HALIDES BASED ON SN1 AND SN2 REACTIVITY

Carmina V. Pena, Martin A. Pineda, Marc C. Punongbayan, Mediatrix B. Saraos, Nympha S. Sia and Bito A. Solima Group 8 2C Medical Technology Organic Chemistry Laboratory

ABSTRACT
Organic halides are organic compounds in which one or more hydrogen atoms have been substituted by a halogen atom. In this experiment we were given objectives to differentiate primary, secondary and tertiary organic halides based on SN reactivity with SN1 and SN2 mechanisms. We were given sample compounds of n-butyl chloride, sec-butyl chloride, tert-butyl chloride and chlorobenzene. All compounds were tested with Alcoholic AgNO 3 which is for SN1 reactivity and with Nal in Acetone which is for SN2 reactivity. In the test for SN1 reactivity, only chlorobenzene didnt react with alcoholic AgNO3 while the other compounds reacted resulting to white precipitate in a time order of tertbutyl chloride being the first, sec-butyl being the second and n-butyl being the last. In the test for SN2 reactivity, again only chlorobenzene didnt react with Nal in Acetone while the other compounds reacted resulting to white precipitate with a time order of n-butyl chloride being the first, sec-butyl chloride being the second and tert-butyl being last.

I. Introduction
Organic halides are organic compounds containing a halogen atom bonded to a carbon (C) atom. Fluorine (F), chlorine (Cl), bromine (Br), and iodine (I) are all types of halogen atoms. If the -carbon atom is tetragonal or sp3 hybridized in the compound, the organic halide can be classified as primary, secondary or tertiary depending on the degree of substitution of hydrogen atom by an R group. Organic halides 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.

are the most reactive and can be converted into many other compounds. Organobromides are less reactive than organoiodides but more reactive than organochlorides. Organofluorides are the least reactive of the organic halides. Reactivity of these types of halides can also be differentiated through a substitution reaction with a nucleophile, depending on which reactant molecule is involved in rate-determining step. If the rate is dependent on the organic halide, the reaction is unimolecular or SN1. If the rate is dependent on the organic halide and the nucleophile then the reaction is bimolecular SN2. In this experiment, to test for S N1 reactivity the samples will be tested using 2% ethanolic AgNO3 and to test for SN2 reactivity the samples will be tested using 15% NaI in anhydrous acetone. Our group must be able to differentiate primary, secondary and tertiary organic halides based on their SN reactivity and be able to differentiate SN1 and SN2 mechanisms with organic halides.

n-butyl chloride -a sample of Primary organic halide

sec-butyl chloride -a sample of secondary organic halide

tert-butyl chloride - a sample of tertiary organic halide

II. Experimental
A. Compounds used n-butyl chloride sec-butyl chloride tert-butyl chloride chlorobenzene 2% Ethanolic AgNO3 15% NaI in anhydrous acetone

The reactivity of organic halides depends on the halogen atom that is bonded to the carbon atom in the particular compound. Organoiodides

B. Procedure 1. SN1 Reactivity: Reaction with Alcoholic AgNO3 Twenty (20) drops of 2% ethanolic AgNO3 were added to four (4) test tubes. Five (5) drops of each sample (n-butyl chloride, sec-butyl chloride, tert-butyl chloride and chlorobenzene) were added to one of the four test tubes prepared containing twenty (20) drops of 2% ethanolic AgNO3. One member of the group was tasked to shake the test tubes and another member was tasked to take note of the time needed for a silver halide precipitate to be produced. 2. SN2 Reactivity: Acetone Reaction with NaI in

the reactant. The three (3) (n-butyl chloride, secbutyl chloride, tert-butyl chloride) organic halides produced a white precipitate, tert-butyl chloride being the first to react with only 4 seconds to precipitate then sec-butyl chloride reacted next having 7 seconds to produce a white precipitate and lastly n-butyl chloride having 11 seconds to precipitate. The kinetics of the reaction is dependent on the alkyl halide. The more stable the carbocation intermediate the faster the rate of SN 1 reactions. Based on these results, we inferred that tertiary organic halides are the highest reactive organic halides during unimolecular nucleophilic or SN1 substitution reactions. Reaction with 5% NaI in anhydrous acetone White precipitate 3 seconds (1st) White precipitate 7 seconds (2nd) White precipitate 9 seconds (3rd)

Sample used

n-butyl chloride Sec-butyl chloride

Four (4) Test tubes to be used were dried-up. Two (2) drops of 15% NaI in anhydrous acetone were added to each dry test tube. Five (5) drops of each sample (n-butyl chloride, sec-butyl chloride, tert-butyl chloride and chlorobenzene) were added to one of the four test tubes prepared containing 15% NaI in anhydrous acetone. One member of the group was assigned to mix the mixtures well and another member was assigned to take note of the time required for a precipitate to form.

Tert-butyl chloride

Chlorobenzene Table 2 (SN2 Reactivity)

No Reaction

III. Results and discussion

Sample used n-butyl chloride Sec-butyl chloride Reaction with 2% ethanolic AgNO3 White precipitate 11 seconds (3rd) White precipitate Turbid solution 7 seconds (2nd) White precipitate 4 seconds(1st) No reaction

Tert-butyl chloride

Table 2 shows the results of the test for SN2 reactivity. Again only chlorobenzene didnt react with Nal in Acetone while the three (3) (n-butyl chloride, sec-butyl chloride, tert-butyl chloride) organic halides produced a white precipitate nbutyl chloride being the first to react with only 3 seconds to precipitate then sec-butyl chloride reacted next having 7 seconds to produce a white precipitate and lastly tert-butyl chloride having 9 seconds to precipitate. The kinetics of this reaction is dependent on th alkyl halide and nucleophile. Based on these results, we inferred that primary organic halides are the highest reactive organic halides during unimolecular nucleophilic or SN1 substitution reactions.

Chlorobenzene Table 1 (SN1 Reactivity)

IV. References
http://www.google.com.ph/search?q=organic+hal ides&ie=utf-8&oe=utf8&aq=t&rls=org.mozilla:enUS:official&client=firefoxa#pq=organic+halides&hl=en&sugexp=gsis%2Ci1 8n%3Dtrue&cp=26&gs_id=16&xhr=t&q=what+is

The table 1 shows the results of the test for S N1 reactivity differentiation of organic halides. Only chlorobenzene didnt react with Alcoholic AgNO3 while the other organic halides have reacted with

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