Copy the figure shown below onto your scratch paper.
Then, complete the figure on your scratch paper by drawing out the intermediates and arrow-pushing mechanism in Boxes 1-3 that explain the formation of the final products shown. You should start your arrow-pushing in Box 1, and you will use all boxes.
Now, report the formal charges (+,0,-) that appear on the alpha carbon, beta carbon, and bromine atoms in each box, and match the contents of each box to a single phrase (A-H) that best describes the mechanistic step that occurs in each box.
A. A hydride shift occurs.
B. A methyl shift occurs.
C. A nucleophile attacks a tertiary carbocation.
D. A leaving group leaves.
E. A nucleophile attacks a secondary carbocation.
F. Br is protonated, the alpha carbon is deprotonated, and a pi bond forms
G. A carbocation attacks the Br.
H. Br is protonated, the beta carbon is deprotonated, and a pi bond forms