The chlorine atom of the following compound t | vedclass

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Question

(A) The reaction between a haloalkane and $AgNO_3$ proceeds via the formation of a carbocation intermediate. The more stable the resulting carbocation

Vedclass · Accepted Answer

$Cl^a$

Vedclass · Answer

(A) The reaction between a haloalkane and $AgNO_3$ proceeds via the formation of a carbocation intermediate. The more stable the resulting carbocation,the more readily the reaction occurs to yield a precipitate of $AgCl$.In the given cyclic ether structure,the $Cl^a$ atom is attached to the carbon atom adjacent to the oxygen atom. Upon the removal of $Cl^a$ as a chloride ion,the resulting carbocation is an oxocarbenium ion,which is significantly stabilized by the resonance effect of the lone pair of electrons on the adjacent oxygen atom $(O-C^+ \leftrightarrow O^+=C)$.This resonance stabilization makes the formation of this specific carbocation much faster and more favorable compared to the other positions $(Cl^b, Cl^c, Cl^d)$,which do not benefit from such direct resonance stabilization by the oxygen atom.Therefore,$Cl^a$ reacts most readily with $AgNO_3$.

The chlorine atom of the following compound that reacts most readily with $AgNO_3$ to give a precipitate is

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