Decide what kind of transformations steps 1-5 are.
?
H-Br (excess)
Me-Li
H
H
Step 1
Step 1
Step 2
H
H
Br
Step 5
?
Br
[Choose]
[Choose]
Proton transfer
1,2-methyl shift
Br
OH2
H
Step 2
Step 3
Loss of leaving group
Step 4
Nucleophilic attack
Step 5
1,2-hydride shift
Step 4
Step Ste 3
?
Br
H