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Experiment # 8 Synthesis and Reactivity of Tert-Butyl Chloride
Experiment # 8 Synthesis and Reactivity of Tert-Butyl Chloride
HCl
OH Cl
H-Cl -H2O Cl
OH OH2 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 SN1
reaction, and the sodium iodide test proceeds via an SN2 reaction.
When a halide is treated with a solution of AgNO3 in ethanol, the silver ion
initially coordinates with the halogen electron pair. This in turn weakens the carbon
halogen bond, and a molecule of insoluble silver halide is formed. The resulting
carbocation reacts with the ethanol to form an ethyl ether. Since this reaction is an SN1
reaction, the order of reactivity for this test tertiary > secondary > primary > methyl.
The sodium iodide test is used to test for the presence of bromine or chlorine.
Alkyl halides that can react by an SN2 mechanism to give a precipitate of sodium halide
salt. The order of reactivity of alkyl halides in this reaction is methyl > primary >
secondary > tertiary.
Procedure:
Glass pipets will be on the bench tops. All chemicals will be in the fume hood. There will
be a ring stand in each fumehood. All aqueous waste can be washed down the drain with
water. Organic liquid waste should go into the waste container that will be in the
fumehood.
Safety Considerations:
- Take care when using the concentrated acid and the silver nitrate solution to not
get it on your skin or clothing. Since we are using a larger volume of concentrated
acid this week, you may want to choose what you wear to lab carefully!
- There will be a waste container for organic liquid waste
- Dispose of used glass pipets in the broken glass container