Question

A. Explain why an Sn2 reaction between diethyl ether and sodium iodide is not favored but...

A. Explain why an Sn2 reaction between diethyl ether and sodium iodide is not favored but an sn2 reaction between diethyl ether and hydrogen iodide is more favorable.

b. explain why the major product of either reaction is not ethene, even with heating

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Answer #1

A. Ethers are less reactive compared to alcohols and alkylhalides due to less leaving group ability of alkoxide ion, but they undergo reaction in presence of acid due to protonation of ether oxygen atom and makes it good leaving group as alcohol. Thus, with NaI diethyl ether do not react but with HI it forms an alcohol and alkyl halide.

B. Because I- is not basic and hence cannot remove proton form ether to form ethene. Reaction of ether with HI, ether first undergo protonation to form protonated ether it subsequently attacked by I- to form alcohol and alkylhalide

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