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Topic: Product of isopropylbenzene + cyclohexene + HF  (Read 11638 times)

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Offline Fzang

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Product of isopropylbenzene + cyclohexene + HF
« on: December 11, 2010, 06:14:51 AM »
That is the question I'm given. No drawings, no clues, no nothing.

Previous question was benzoic acid + nitric acid/sulfuric acid which adds a meta-directed nitro-group to the benzoic acid. Simple as that... but the question in topic... I have no idea. Does it mean I add hydroflouric acid to cyclohexene to create some flourocyclohexane which can then (somehow) react with isopropylbenzene.. or what?

I'm clueless. Every other question in this section follows the "A + B with condition C", except the one in topic.
« Last Edit: December 11, 2010, 06:50:40 AM by Fzang »

Offline Fzang

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Re: Product of isopropylbenzene + cyclohexene + HF
« Reply #1 on: December 11, 2010, 08:09:22 AM »
Maybe this?





That would make perfect sense... I think.

If that's the case, could anybody explain the reaction mechanism, showing the intermediates formed?

Offline ooosh

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Re: Product of isopropylbenzene + cyclohexene + HF
« Reply #2 on: December 13, 2010, 04:23:07 AM »
Dont you know the mechanism of F-C alkylation?

Offline Fzang

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Re: Product of isopropylbenzene + cyclohexene + HF
« Reply #3 on: December 13, 2010, 06:07:44 AM »
HF attaches to the double bond, creating flourocyclohexane.

Flourocyclohexane is converted to cyclohexane-carbocation with AlF3.

Carbocation reacts o/p with benzene isopropylbenzene.

Proton is removed from the o/p located carbon, restoring charge.

Proton regenerates AlF4- to AlF3 and HF.

Is this correct?

Offline Fzang

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Re: Product of isopropylbenzene + cyclohexene + HF
« Reply #4 on: December 13, 2010, 07:14:00 AM »
(Why can't I edit my posts?)

Correction to above. I think HF can create an electrophile/nucleophile by itself without a catalyst. Catalysts are only needed for pure halogens such as Br2.

Offline ooosh

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Re: Product of isopropylbenzene + cyclohexene + HF
« Reply #5 on: December 14, 2010, 10:48:54 PM »
See,you can solve it yourself.

cupid.callin

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Re: Product of isopropylbenzene + cyclohexene + HF
« Reply #6 on: December 15, 2010, 09:14:54 AM »
Its pretty simple example of freidal craft's alkylation.
But the ortho product will be in negligible amount due to steric hindrance .

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