Will bridged compounds the undergo SN1 reaction?
Very interesting question… I would give two answers, at different levels:


At undergrad level, I think the carbenium ion formed at the bridge head is less stabilized that “regular” ternary carbenium ions, because it cannot adopt the planar trigonal geometry which would be ideal for it.
At higher level, this is much more complicated: the norboryl cation is an example of non-classical ion…