CLASSIFICATION OF ORGANIC HALIDES

Carina Lyn D. Batol, Karen Rachel Joyce A. Birol, Alfonso Pio P. Calimag, Justin L. Canasa, Red Aian N. Caragdag Group 3 2A Medical Technology Organic Chemistry Laboratory

ABSTRACT
Organic Halides are organic compounds in which one or more of its hydrogen atoms are substituted by a halogen atom. Unlike other organic compounds, organic halides are synthethic, they are also nonflammable. The main objective of thi s experiment is to dif feren tiate primary, secondary, and tertiary organic h alides based on th ei r S N activity and make a distin cti on between SN1 and S N 2 mechani sms with organi c halides. Th e organic compounds, n-butyl chloride, sec-butyl chloride, tert-butyl chloride and chlorobenzene, were subjected to Beilstein test an d were reacted with eth an olic AgNO 3 an d NaI in anh ydrou s aceton e respectively to classify th em according to th e type of organic h alide th ey bel on g. Th e Beils tein test was con du cted by dipping the prepared nichrome wire to the samples and heating them. All samples produced a green flame proving that they contain Cl in their structures. The samples were, then, reacted with ethanolic AgNO 3 a n d a f o r m a t i o n o f w h i t e p r e c i p i t a t e w a s o b s e r v e d i n t e r t - b u t y l c h l o r i d e while nbutyl chloride, s e c - b u t y l c h l o r i d e a n d chlorobenzene showed no reaction. Finally, the samples were reacted with NaI in anhydrous acetone and all compounds produced a white precipitate, except tertbutyl chloride. The results observed proved that SN1 reaction favors tertiary substrates while the SN2 reaction favors primary and secondary substrates.

INTRODUCTION
Organic halides are organic compounds in which one or more hydrogen atoms are substituted by a halogen atom. This halogen could either be chlorine, bromine, iodine, or fluorine. These organic halides are mostly synthetic and inflammable. The carbon atom attached to the halogen atom is called the alpha carbon. The alpha carbon can be classified as primary, secondary, or tertiary, depending on how many carbon are attached to it, provided that it is an sp3 hybridize carbon. Nucleophilic substitution is a reaction in which the electron donor, or the Nucleophile (Nu) with the electron acceptor or the Electrophile (E) A substitution implies that one group replaces another

There are two fundamental events in these substitution reactions: 1. formation of the new bond to the nucleophile 2. breaking of the bond to the leaving group Depending on the relative timing of these events, two different mechanisms are possible: Bond breaking to form a carbocation preceeds the formation of the new bond : SN1 reaction Simultaneous bond formation and bond breaking : SN2 reaction

SN1 mechanism SN1 indicates a substitution, nucleophilic, unimolecular reaction , described by the expression rate = k [R-LG] This pathway is a multi-step process with the following characteristics:

Figure 1.

step 1: rate determining (slow) loss of the leaving group, LG, to generate a carbocation intermediate, then

step 2: rapid attack of a nucleophile on the electrophilic carbocation to form a new s bond

RESULTS AND DISCUSSION

Sample Condensed Structural Formula

EXPERIMENTAL
A. Compound/s Tested The compounds tested were chlorobenzene, nbutyl chloride, sec-butyl chloride, and tert-butyl chloride. B. Procedure The experiment requires test tubes, matches, copper wires, Bunsen burner, 2% ethanolic AgNO3, copper oxide (optional), calibrated droppers, test tube rack and holder, 15% NaI in anhydrous acetone. 1. Beilstein Test: Copper Halide Test A small loop was made in the copper wire. The loop was heated directly on the oxidizing zone of a non-luminous flame until the green color imparted into the flame disappeared. The copper wire is then cooled, and dipped into the samples. The loop is heated in the non-luminous flame, first in the inner zone, then in the outer zone near the edge of the flame. A green or bluegreen flame indicates the presence of chlorine, bromine, or iodine. 2. SN1 Reactivity: Reaction with Alcoholic AgNO3 5 drops of the sample is added to 20 drops of 2% ethanolic AgNO3. The mixture is shaken and the time for a silver precipitate is recorded. Color of precipitate is also noted. 3. SN2 Reactivity: Reaction with NaI in Acetone In dry test tubes, 5 drops of the sample is added to 2 drops of 15% NaI in anhydrous Acetone. The contents are mixed and the time for precipitate to form and its color is noted. n-butyl chloride

Sec-butyl chloride

Tert-butyl chloride

Chlorobenzene

Table 1. Properties of Alkyl Halides

Samples

Result of Beilstein Test Green Green Green Green

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

Table 2. Beilstein Test Result All the test samples yielded a green flame when put under the Beilstein Test indicating the presence of a halide. Also the Structural Formulae of the samples clearly shows the presence of halides.

Samples

Reaction with 2% ethalonic AgNO3 No Precipitate No Precipitate White Precipitate (1.5 seconds) No Precipitate

REFERENCES
[1] Bayquen, A.V., Cruz, C.T., de Guia,R.M, Lampa, F.F., Pea, G.T., Sarile, A.S.and Torres, P.C. (2009),Laboratory Manual inOrganic Chemistry,C&E Publishing, Inc [2]http://www.mhhe.com/physsci/chemistry/care y/student/olc/ch04nucle.html Date: Spetember 16, 2012

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

Table 3. Reaction with 2% ethalonic AgNO3 The results show that for the S N1 reaction, a tertiary alpha carbon would be more reactive than a secondary, or primary (3>2>1>CH3). Reaction with 15% NaI in anhydrous acetone White Precipitate (3 seconds) White Precipitate (5 seconds) No Precipitate

Samples

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

White Precipitate (7 seconds) Table 4. Reaction with 15% NaI in anhydrous acetone

The results show that for the SN2 reaction, a primary alpha carbon would be more reactive than a secondary, or primary (CH3>1>2>3).