A reluctant first-order substrate can be forced to ionize by adding some silver nitrate (one of the few soluble silver salts) to the reaction. Silver ion reacts with the halogen to form a silver halide (a highly exothermic reaction), generating the cation of the alkyl group.

Give mechanisms for the following silver-promoted rearrangements.
(a)

(b)

Transcribed Image Text:

CHi CH3 AgNO3. H2O CHC-CH-CH он СНЗ CH2l AgNO3, H2O/CH,CH2OH