Which of the following compounds will form the precipitate with aq .   AgNO 3 solution most readily?

Which of the following compounds will form the precipitate with aq. AgNO3 solution most readily?

Solution

It is an example of SN1 reaction.

Rate of SN1 reaction α stability of carbocation 

In option 1 carbocation formed after removing halogen is destabilized by -I effect.

In option 2 carbocation formed after removing halogen is stabilized by +M effect since lone pair is present at oxygen atom.

In option 3 carbocation formed after removing halogen is stabilized by +M effect of lone pair present on nitrogen atom but lone pair is also in conjugation with benzene ring therefore +M effect is less.

In option 4 carbocation formed after removing halogen is stabilized by +M effect of lone pair present on nitrogen atom and +M effect of nitrogen atom is more than that of oxygen atom. Hence, option 4 is most stable. 

Asked in: JEE Main 2020 (04 Sep Shift 2)

Practice more General Organic Chemistry questions on Aicharya