3D1CC766213F428C812619271266227D - Experiment # 8 Synthesis...

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Experiment # 8 Synthesis and Reactivity of tert -Butyl Chloride Introduction: The purpose of this experiment is to synthesize tert -butyl chloride via an S N 1 reaction and to characterize it using simple chemical tests to describe its reactivity. HCl tert -butyl alcohol tert -butyl chloride OH Cl Tertiary alcohols can easily be converted to their corresponding alkyl chlorides by the addition of concentrated hydrochloric acid to the alcohol. In this experiment, concentrated hydrochloric acid is used to prepare tert -butyl chloride from tert -butyl alcohol via S N 1 reaction. The mechanism of this S N 1 reaction involves three steps. First, is the rapid (and reversible) protonation of the alcohol, followed by the much slower rate-determining step, the loss of water to give a relatively stable tertiary carbocation. In the final step, the carbocation is rapidly attacked by the chloride ion to form the alkyl halide. The alkyl halide is insoluble in water, and thus it separates from the aqueous layer. OH OH 2 Cl H-Cl -H 2 O Cl Characterization of alkyl halides takes advantage of the fact that the halogen can easily be displaced. The two tests that you will use are complementary, and are useful for classifying the structure of alkyl halides. The silver nitrate test proceeds via an S N 1 reaction, and the sodium iodide test proceeds via an S
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This note was uploaded on 02/02/2012 for the course CHEM 211 taught by Professor Santos,j during the Spring '11 term at Abu Dhabi University.

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3D1CC766213F428C812619271266227D - Experiment # 8 Synthesis...

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