Friday, 17 July 2015

organic chemistry - Why do t-butyl bromide and silver(I) nitrite form the nitroalkane, not the nitrite ester?


We know that reaction of $\ce{AgNO2}$ with alkyl halides is SN1 type reaction and follows HSAB principle. So in the reaction of $\ce{(CH3)3C Br}$ we would expect $\ce{AgBr}$ to form and also a carbocation $\ce{(CH3)3C+}$.


According to HSAB, since the electrophile is hard, we expect the hard nucleophile to attack. So attack is expected from oxygen, and expected product is $\ce{(CH3)3C-ONO}$


But my book states that reaction product is $\ce{(CH3)3C-NO2}$. Why is this product formed?




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