For each problem below, draw the intermediate that you get after pushing the arrows. In which of the following pairs is the intermediate a carbocation?
(a)
(b)
(c)
(d)

Question

For each problem below, draw the intermediate that you get after pushing the arrows. In which of the following pairs is the intermediate a carbocation? (a) (b) (c) (d)

TestHub · Accepted Answer

(a) The C-Br pair leaves with Br - , forming a tertiary carbocation and Br - . (b) HO - adds to the carbonyl carbon, and the π pair moves onto O, forming a tetrahedral intermediate. (c) The π bond attacks Br 2 , and the Br-Br pair leaves with the far Br, forming a tertiary cation and Br - . (d) Water opens the bromonium ion as the C-Br pair moves onto Br, forming protonated 2-bromoethanol. Answer: (B)

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