Synthesis of an Alkyl Halide
SYNTHESIS OF AN ALKYL HALIDE
S.M. BLANCAFLOR1
1INSTITUTE OF BIOLOGY, COLLEGE OF SCIENCE
UNIVERSITY OF THE PHILIPPINES, DILIMAN, QUEZON CITY 1101, PHILIPPINES
DATE SUBMITTED: 3 JANUARY 2012
DATE PERFORMED: 8 DECEMBER 2011
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ABSTRACT
Alkyl halides are molecules which have a carbon atom attached to a halogen atom (e.g., chlorine, iodine, or bromine.) Alkyl halides are very important since they are used in many of the products used today. They can be synthesized by means of adding alcohols to hydrogen halides (such as HCl, HI, or HBr) resulting in nucleophilic substitution (specifically the SN1 reaction.) The experiment was done with the goal of synthesizing an alkyl halide from alcohol and a hydrogen halide. In order to do this, tert-butyl alcohol was mixed with HCl to form crude tert-butyl chloride. Solid NaHCO3 and CaCl2 were used to prevent possible hydrolysis of the product. It was then purified through distillation. Results confirm the successful production of 5.01 g (51.5% yield) of the alkyl halide, tert-butyl choride.
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INTRODUCTION
The importance of alkyl halides is great as it can be used in making pharmaceuticals, Teflon pans, flame retardants, fire extinguishers, solvents, and propellers [1][2] and other things used on a daily basis. However, they are pollutants that cause serious damage to the ozone layer. Nevertheless, they are invaluable since they can also be used as intermediates to produce other functional groups (e.g., amines, esters, and alkenes).
Alkyl halides have the general formula RX (where R= alkyl/substituted alkyl group and X = F, Cl, Br, or I.) They are insoluble in water and sulfuric acid and are soluble in organic solvents.[3] They are synthesized for their many uses.
There are several ways by which alkyl halides can be synthesized. Some of those are halogenation of alkanes with Cl2 or Br2, addition of HX to
S.M. BLANCAFLOR1
1INSTITUTE OF BIOLOGY, COLLEGE OF SCIENCE
UNIVERSITY OF THE PHILIPPINES, DILIMAN, QUEZON CITY 1101, PHILIPPINES
DATE SUBMITTED: 3 JANUARY 2012
DATE PERFORMED: 8 DECEMBER 2011
-------------------------------------------------
ABSTRACT
Alkyl halides are molecules which have a carbon atom attached to a halogen atom (e.g., chlorine, iodine, or bromine.) Alkyl halides are very important since they are used in many of the products used today. They can be synthesized by means of adding alcohols to hydrogen halides (such as HCl, HI, or HBr) resulting in nucleophilic substitution (specifically the SN1 reaction.) The experiment was done with the goal of synthesizing an alkyl halide from alcohol and a hydrogen halide. In order to do this, tert-butyl alcohol was mixed with HCl to form crude tert-butyl chloride. Solid NaHCO3 and CaCl2 were used to prevent possible hydrolysis of the product. It was then purified through distillation. Results confirm the successful production of 5.01 g (51.5% yield) of the alkyl halide, tert-butyl choride.
-------------------------------------------------
INTRODUCTION
The importance of alkyl halides is great as it can be used in making pharmaceuticals, Teflon pans, flame retardants, fire extinguishers, solvents, and propellers [1][2] and other things used on a daily basis. However, they are pollutants that cause serious damage to the ozone layer. Nevertheless, they are invaluable since they can also be used as intermediates to produce other functional groups (e.g., amines, esters, and alkenes).
Alkyl halides have the general formula RX (where R= alkyl/substituted alkyl group and X = F, Cl, Br, or I.) They are insoluble in water and sulfuric acid and are soluble in organic solvents.[3] They are synthesized for their many uses.
There are several ways by which alkyl halides can be synthesized. Some of those are halogenation of alkanes with Cl2 or Br2, addition of HX to
References: [3]Shirley, D.A., 1964. Organic Chemistry. USA: Holt, Reinhart, and Winston Inc. 197. [4][6] Meislich, H., 1999. Theories and Problems of Organic Chemistry. USA: McGraw-Hill. 119,123. [5] Bloch, P.R., 2006. Organic Chemistry Demystified. USA: McGraw- Hill. 258.