Problem: When tert-butyl bromide undergoes SN1 hydrolysis, adding a “common ion” (e.g., NaBr) to the aqueous solution has no effect on the rate. On the other hand, when (C6H5)2CHBr undergoes SN1 hydrolysis, adding NaBr retards the reaction. Given that the (C6H5)2CH+ cation is known to be much more stable than the (CH3)3C+ cation (and we shall see why in Section 15.12A), provide an explanation for the different behavior of the two compounds.  

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When tert-butyl bromide undergoes SN1 hydrolysis, adding a “common ion” (e.g., NaBr) to the aqueous solution has no effect on the rate. On the other hand, when (C6H5)2CHBr undergoes SN1 hydrolysis, adding NaBr retards the reaction. Given that the (C6H5)2CH+ cation is known to be much more stable than the (CH3)3C+ cation (and we shall see why in Section 15.12A), provide an explanation for the different behavior of the two compounds.
 

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Solomons 10th Edition. You can also practice Organic Chemistry - Solomons 10th Edition practice problems.