Destroyer 2013 Orgo #141

[DrRoyal Pains]

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For # 141 in orgo, why is there a hydride shift? I understand the mechanism, but I don't understand WHY. Is it because when you add 3 or more carbons in a linear fashion, you get rearrangement?

 

[jHoon]

With the hydride shift you get a tertiary carbocation meaning a more stable intermediate. That's what you get t-butylbenzene instead of isobutylbenzene

 

[DrRoyal Pains]

I understand that. But is what I said true? About having rearrangement with 3 or more carbons. I read it somewhere, just forget where. Im pretty sure it was in Destroyer.

 

[Illfavor]

I understand that. But is what I said true? About having rearrangement with 3 or more carbons. I read it somewhere, just forget where. Im pretty sure it was in Destroyer.

I had only ever seen that in Destroyer.

 

[john616]

AlCl3 picks up the halogen from the alkyl halide,which creates a carbocation, and if it can rearrange to get more stable, it will. I think this is the Friedel Crafts alkylation.

 

[DrRoyal Pains]

Gotcha. Thanks everyone!

AlCl3 picks up the halogen from the alkyl halide,which creates a carbocation, and if it can rearrange to get more stable, it will. I think this is the Friedel Crafts alkylation.