1. Treatment of tert-butyl iodide or tert-butyl chloride in 80% aqueous ethanol gives the same ratio of substitution and elimination products. In these reactions, Hâ‚‚O serves as the nucleophile or base whereas ethanol (EtOH) is the solvent.
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Indicate which of the compounds will give a higher substitution-product to elimination-product ratio when it reacts with isopropyl bromide: ethoxide ion or tert-butoxide ion.
(a) Consider the general problem of converting a tertiary alkyl halide to an alkene, for example, the conversion of tert-butyl chloride to 2 -methylpropene. What experimental conditions would you choose to ensure that elimination is favored over substitution? (b) Consider the opposite problem, that of carrying out a substitution reaction on a tertiary alky / halide. Use as your example the conversion of tert-butyl chloride to tert-buryl ethyl ether. What experimental conditions would you employ to ensure the highest possible yield of the ether?
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