Preparation and Purification of an Alkyl Halide
Salazar, Anna Flora Natividad C.
Institute of Biology, University of the Philippines, Diliman, Quezon City Date Performed: 17 September 2014
Date Submitted: 26 September 2014
This experiment aims to show how an alkyl halide is obtained from an alcohol a hydrogen halide. Here, tert-butyl alcohol and HCl were used to yield tert-butyl chloride. To synthesize this, tert-butyl alcohol and HCl were mixed in a separatory funnel. When the organic layer was obtained, it was then purified through the method of simple distillation.
Alkyl halides, also known as haloalkanes, are a functional group of chemical compounds. The distinguishing characteristic of this particular group is that a halogen, or more than one halogen, is attached to an alkane.
Among the many ways developed to synthesize an alkyl halide, the most common method is synthesis by the reaction between an alcohol and a hydrogen halide. The type of reaction that occurs between the two is called a nucleophilic substitution, wherein the hydrogen halide serves as the nucleophile, or the electron pair donor, and the alcohol serves as the electrophile, or the electron pair acceptor, producing water and the desired alkyl halide.
The reactivity of a hydrogen halide with alcohol can be directly related to the atomic weight of the halogen. When arranged in order of increasing atomic weight, the hydrogen halides are also arranged in order of increasing reactivity. That is, HF < HCl < HBr < HI, where HI contains the halogen with the greatest atomic weight, and is the most reactive one with alcohol as well.
Synthesis of tert-butyl chloride was done with the use of a 50mL separatory funnel. In this funnel, 10mL tert-butyl alcohol and 20mL cold concentrated HCl were placed. The mixture was swirled gently, without being shaken. Internal pressure was relieved by slowly opening the...
References: VI. Appendices
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