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Write Brief Answer · Q20

Q.Predict the products when bromoethane is treated with the following: i) KNO₂ ii) AgNO₂

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Step 1. The nitrite ion, NO2-, is an ambident nucleophile -- it can attack through either its oxygen or its nitrogen atom, and which one dominates depends on the counter-ion/reagent used.

Step 2 (i). With potassium nitrite (an essentially ionic reagent), attack proceeds through OXYGEN, giving the ester-like alkyl nitrite: bromoethane + KNO2 gives ethyl nitrite (CH3CH2-O-N=O) + KBr.

Step 3 (ii). With silver nitrite (Ag-O bonding being more covalent, which favours reaction through the other, nitrogen, end instead), attack proceeds through NITROGEN, giving the nitroalkane directly: bromoethane + AgNO2 gives nitroethane (CH3CH2-NO2) + AgBr. …

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