8 Which of the following syntheses is the best method for ma

8. Which of the following syntheses is the best method for making tert-butoxybenzene? OH CH O: CH3 H,PO, (aq) + CH3-C-OH CH3 3-C-OH A. CH B. O: CH3 CH3-C-OH CH C. CH3 D. CH 19. What of the following reactions will not produce the epoxide 2-methyl-3-phenyloxirane? ONa CH3-CH-CH-OTs HO CH3 CI B. OH CH H,SO,(aq) 60 °C OH OH D. CH-C-0OH

Solution

8.

Answer is option (A)

Since the alcohol is a tertiary alcohol, it will produce a tertiary carbocation (which is the most stable carbocation). SN1 reaction mechanism is best suited for the tertiary group. So, the lone pair on the oxygen atom of the phenol can attack the tertiary carbocation thereby by forms tet-butoxybenzene.

9.

Answer is option (D)

In option (A-C) there is a good leaving group present to form an epoxide. For option (E) when alkene reacts with peracid it forms an epoxide.