[Paulie]

Hello, I am studying for my organic chemistry exam in 3 days, and have a few questions. Hoping for as many answers as possible

1) Does anyone have the mechanism for oxidation of the methyl group to carboxylic acid by KMnO₄?

2) What happens in this reaction? : Isobutylbromide + (CH₃)₃CO^-  Isobutylene

3) In Friedel-Crafts acylation, if you simply want to end up with an alkane, is it necessary to use an acyl halide? Can't one just use the corresponding alkyl halide and skip the Clemmensen reduction to remove the oxygen afterwards?

Thanks in advance

[fledarmus]

In response to 3) - think about reactivity of the starting material and the desired product of your reaction to a Friedel-Crafts reaction. What sort of substituent is an alkyl group? An acyl group?

In response to 2) - draw the structures of isobutylbromide and isobutylene. How are they related?

In response to 1) - which methyl group? Are you thinking of toluene being oxidized to benzoic acid?

[orgopete]

1) Its complicated and I always use a mixture of mechanisms. None the less, they start with formation of a radical. Can a radical form from toluene?

3) What are the products of 1-bromobutane, benzene, and AlCl3?