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Question 64 of 76

Q.When ethyl iodide is treated with dry silver oxide it forms :

(a) Diethyl ether
(b) Ethyl methyl ether
(c) Ethyl alcohol
(d) Silver ethoxide
Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2019MCQ· 1mImportance★★★★★
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Two molecules of ethyl iodide react with dry Ag2OAg_2O to give diethyl ether, with AgIAgI as the by-product.

Dry silver oxide is a classical reagent for converting alkyl halides into ethers: 2C2H5I+Ag2O→(C2H5)2O+2AgI2C_2H_5I + Ag_2O \rightarrow (C_2H_5)_2O + 2AgI. Mechanistically, the oxide oxygen of Ag2OAg_2O displaces iodide from one ethyl iodide molecule (assisted by the strong affinity of Ag+Ag^+ for I−I^-, which drives the reaction), generating an intermediate silver ethoxide/alkoxide species that then reacts with a second molecule of ethyl iodide in a Williamson-type SN2S_N2 step, giving the symmetrical ether C2H5−O−C2H5C_2H_5-O-C_2H_5. Option (d), silver ethoxide, is only the transient intermediate, not the isolated pro …

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