# If ethyl bromide is treated with alcoholic silver nitrate, which product will be formed? [duplicate]

Silver nitrate promotes ionisation , so the ethyl bromide should ionise, the alcoholic species should attack (by loan pair of oxygen) so finally an ether should be formed , but the answer given in my book is nitroethane and ethyl nitrite.

• Do you mean ethyl nitrile ($\ce{CH3CH2CN}$) or ethyl nitrite ($\ce{CH3CH2ONO}$)? I find it hard to see how ethyl nitrile could be formed at all. Jan 21 '18 at 16:56
• The book probably assumes that the 'alcohol' is not a very nucleophilic one, so the nitrate ion attacks; and as the nitrate ion is bidentate... Everything adds up, except for the alcohol not participating at all; I'd also have thought it would do something, but there you go. Jan 21 '18 at 17:39
• @user6376297 how nitrate can add to form nitroethane, this is my confusion, I can see formation of nitroethane when nitrite is used, but when nitrate is used , how nitroethane form ?
– user49956
Jan 21 '18 at 17:42
• Jan 21 '18 at 17:44
• @Mithoron, the dupe question is alkyl halide + silver "nitrite" but this question specifically asks about silver "nitrate". Jan 22 '18 at 5:18