You are asked to synthesize the monosubstituted benzene derivative shown below a

Question

You are asked to synthesize the monosubstituted benzene derivative shown below as the Final product of Scheme 3 (3-methyl-1-phenylbutane). You do not get a good yield via Friedel-Crafts alkylation due to rearrangement. The only chemicals you have access to are given in the table. Fill in the blank with the corresponding letter in the table and draw the skeletal structure for each indicated species below:

I believe I need to use a Gilman Reaction for scheme 3, and the two starting species should be benzene (A) and 3-methyl-1-butene(B). However it said I was wrong when I tried to brominate the 3-methyle-1-butene for scheme 2. I lose a lot of points for each wrong step! Please help.

Explanation / Answer

1. B 2. D 3. 1-bromo-3-methylbutane 4. C 5. 1-lithium-3-methylbutane (yes I know this is improper but I'm unsure of the naming of the lithium branch) 6. E 8. A 9. G 10. 1-bromobenzene

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