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Question

What are the products of the following reaction?



A

The reaction proceeds via the SN2 mechanism

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B

The reaction involves a carbocation

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C

The reaction involves a carbocation rearrangement

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D

The reaction is driven forward by the formation of a silver halide

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Solution

The correct options are
B

The reaction involves a carbocation


C

The reaction involves a carbocation rearrangement


D

The reaction is driven forward by the formation of a silver halide


Strange combination – a primary alkyl halide, AgNO3 and polar protic solvents. The solvent suggest that the reaction is SN1 and yet we have
a primary substrate and no proper/tough nucleophile. It is certainly a hydrolysis – assuming water is in excess. Ag+ salts tend to accelerate
the ionization. The following intermediate is observed, which undergoes rearrangement:

Now, the solvent molecule - which is also a nucleophile attacks the carbocation:


Chemistry

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