Below is a problem I got stuck at in a test .
The first compund in this chain was easy to figure out , it was something like this :
Then I had this intermediate compound for B.(I didn't add the bromide anion because this is where my confusion starts)
Now ,here it shouldn't be correct to do a hydride shift outside the ring as it would result in a much less stable carbocation . But if I proceed using that idea and solving further for part D and E , I am getting option (b) as my answer and the correct answer is option (d). Although if I do a hydride shift there then that opens a way for a ring expansion and hence a correct answer (according to the answer key) .