[webassignbuddy]

You are asked to synthesize the molecule below starting with benzene as the source of the 6-membered ring and any other reagents you need. Using the reagents listed on the reagent sheet, write the corresponding letter designations from the reagent sheet of the reagents you would use in the order you would use them (separate each with a comma) to synthesize the given major organic product in 4 steps.





This is what I did, going backwards.

4. Z (Birch's reduction)
3. CC (Bromination)
2. AA (Benzene Oxidation)
1. I thought it would be friedel's crafts ALKYLATION with CH₃–Cl / AlCl₃ but that isn't even in the table.

This is driving me crazy - it's my last problem and I just want to get it over with!

[Vidya]

whats wrong if we follow :
DD--AA--CC

[webassignbuddy]

whats wrong if we follow :
DD--AA--CC

Are you saying DD would be our first reagent? that gives us isopropylbenzene, which has one benzylic hydrogen...which I guess could then be oxidized, using AA, to the benzoic acid, right?

Also, is the last step birch reduction?

[webassignbuddy]

whats wrong if we follow :
DD--AA--CC

Sweet! The answer IS DD,AA,CC,Z!
Thanks a bunch! 

[Altered State]

Won't DD reaction produce polyalkylation?