Question

13 SN1: Synthesis of tert-Butyl Chloride Alkyl halides can be prepared from their corresponding alcohols via an acid catalyzed substitution reaction. The mechanism of these acid catalyzed substitution reactions are labeled as SNI (substitution, nucleophilic, unimolecular) and S 2 (substitution, nucleophilic, bimolecular). Tertiary alcohols follow the Syl route, primary alcohols follow the Sy2 route, and secondary alcohols can follow either path. Under acidic conditions, the mechanism (Figure 1) of the Syl reaction involves rapid protonation of the alcohol, followed by the loss of water as the rate-determining step. This generates a relatively stable carbocation which is then attacked by the halide ion to form the alkyl halide. Sy reactions are favored by tertiarry alcohols because they tend to form more stable carbocations. сн CH3 CHн CH - Но н н,стон Hас Cr Hстон, Hас нса Нас Нас сн, Figure 1 Comnversion of t-butanol into t-butyl chloride by an Syl mechanism The product will be verified by gas chromatography by comparing the chromatograms of the starting material, tert-butyl chloride standard, and your product. Confirmation of your product, tert-butyl chloride, can also be performed by reacting the product with a solution of silver nitrate in ethanol. The tertiary alkyl halide will react by means of an Syl mechanism with the silver nitrate to form an insoluble silver halide. The appearance of a precipitate indicates a positive result indicating the presence of a tertiary alkyl halide. ОВJЕCTIVES In this experiment, you Synthesize tert-butyl chloride via an SNl reaction. Confirm the presence of a tertiary alkyl halide using the silver nitrate test. Verify the product by gas chromatography. will MATERIALS Part I Synthesis of tert-Butyl Chloride two 10 mL glass vials and caps hydrochloric acid, concentrated tert-butanol, reagent grade saturated sodium bicarbonate solution saturated sodium chloride solution sodium sulfate, anhydrous DI water 25 mL graduated cylinder 10 mL graduated cylinder 50 mL beaker 250 mL beaker 125 mL Erlenmeyer flask separatory funnel apparatus glass funnel disposable Pasteur pipets and bulb ice

Answer 1

Angwer! - son 9 @ here Poctonation of an alcomal generates alkyloxonium it et is es hech the con om, abbreviated as RTOM, CM3 when leady to formation SNI nucleophetic substitution of carbocation In the first step. yeg as it leads to the formation of intermediate (Cambocation) a planar molecule naving Spa 0 SNI ( carbocaten is configuraton B @ ci© ② (CH3C-OM 6 4 Saturated sodiem chloride Solceton (CM3 / 3 C-Cl + H2O t. Nach CM My C-,C-04 3 CM3 MC-Ć-cl cm3 2- chloro-2-methyl propane 2-methyl prepan-2-ol