Which of the following compounds will form the precipitate with aq. AgNO3 solution most readily?
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The Correct Option is B
Solution and Explanation
In (1) the cation \(\mathrm{CH_3CH_2O{=}CH_2^+}\) is stabilised by the oxygen lone pair, but oxygen is more electronegative than nitrogen, so it is a weaker donor.
In (3) the nitrogen lone pair is delocalised into the benzene ring, so it is less available to stabilise the cation.
In (4) Br is on the beta carbon; ionisation needs neighbouring-group participation to give a strained aziridinium ion, and the lone pair is also delocalised into the aryl ring, so it is slower than direct alpha ionisation.
In (2) the nitrogen lone pair of the piperidine ring is fully available (not conjugated with any pi system) and gives the very stable iminium ion \(\mathrm{R_2N^+{=}CH_2}\). Hence (2) ionises most readily.
Answer: (2) N-(bromomethyl)piperidine
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