First slide

Organic reagents and intermediates

Question

Of the following order of reactivity of Cl with AgNO₃, which one is correct?

Moderate

A

CH₂ = CH –CH₂Cl > CH₃CH₂CH₂Cl > CH₃CH =CHCl
B

CH₂ = CH –CH₂Cl > CH₃CH₂CH₂Cl < CH₃CH =CHCl
C

CH₂ = CH –CH₂Cl < CH₃CH₂CH₂Cl > CH₃CH =CHCl
D

CH₂ = CH –CH₂Cl < ${CH}_{3} {CH}_{2} {CH}_{2} Cl$ < CH₃CH =CHCl

Solution

${CH}_{2} = {CHCH}_{2} Cl$ is an allylic chloride that reacts with ${AgNO}_{3}$ in the cold to give a white precipitate of $AgCl$ . ${CH}_{3} {CH}_{2} {CH}_{2} Cl$ gives a precipitate on warming.
${CH}_{3} CH = CHCl$ is a vinylic chloride which is inert even when heated.
Hence, the correct answer is (1).

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