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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.

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  • $\begingroup$ 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. $\endgroup$ – Ben Norris Jan 21 '18 at 16:56
  • $\begingroup$ 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. $\endgroup$ – user6376297 Jan 21 '18 at 17:39
  • $\begingroup$ @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 ? $\endgroup$ – Rishabh Sharma Jan 21 '18 at 17:42
  • $\begingroup$ related chemistry.stackexchange.com/questions/88515/… $\endgroup$ – Mithoron Jan 21 '18 at 17:44
  • $\begingroup$ @Mithoron, the dupe question is alkyl halide + silver "nitrite" but this question specifically asks about silver "nitrate". $\endgroup$ – Nilay Ghosh Jan 22 '18 at 5:18

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