Which of the following compounds will not pro | vedclass

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Question

(A) The reaction with $AgNO_3$ involves the formation of a carbocation intermediate. Compounds that form stable carbocations react readily to produce

Vedclass · Accepted Answer

$1-$Bromocyclohexene

Vedclass · Answer

(A) The reaction with $AgNO_3$ involves the formation of a carbocation intermediate. Compounds that form stable carbocations react readily to produce a precipitate of $AgBr$.$A$. $1$-Bromocyclohexene: The bromine atom is attached to an $sp^2$ hybridized carbon atom of a double bond (vinylic halide). The resulting vinylic carbocation is highly unstable due to the high electronegativity of the $sp^2$ carbon and the inability to stabilize the positive charge through resonance. Therefore,it does not react with $AgNO_3$ to form a precipitate.$B$. Benzyl bromide: Forms a resonance-stabilized benzyl carbocation,which reacts readily.$C$. $3$-Bromocyclopropene: Forms a cyclopropenyl cation,which is aromatic ($2\pi$ electrons) and highly stable.$D$. $3$-Phenyl-$3$-bromoprop-$1$-ene: Forms a resonance-stabilized carbocation (allylic and benzylic stabilization).Thus,$1$-Bromocyclohexene is the correct answer.

Which of the following compounds will not produce a precipitate on reaction with $AgNO_3$?

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