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Topic: Puzzling Benzene Transofrmation  (Read 5474 times)

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Offline Ariana

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Puzzling Benzene Transofrmation
« on: July 19, 2009, 06:18:37 PM »
Please see attached file.

You can only use starting materials of 4 carbons or less for the transformation.

Any type of help/hints/ideas will be appreciated =].
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Offline Borek

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Re: Puzzling Benzene Transofrmation
« Reply #1 on: July 19, 2009, 06:40:09 PM »
Please read forum rules.
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Offline Ariana

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Re: Puzzling Benzene Transofrmation
« Reply #2 on: July 19, 2009, 07:30:12 PM »
Read. I suppose you're asking me to show an attempt at the problem?

Please see attached file again. I get the bottom part alright. I'm just confused about incorporating the top part -__-. And if there's a different way to do this. etc
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Offline AWK

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Re: Puzzling Benzene Transofrmation
« Reply #3 on: July 20, 2009, 06:55:03 AM »
The method with BH3 will not work in this case
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Offline Ariana

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Re: Puzzling Benzene Transofrmation
« Reply #4 on: July 21, 2009, 06:46:00 PM »
Aah yea. I must have been sleepy when doing that =P. Anyway, here's the solution. There's only a slight problem at step 10 where an anti-markovnikov addition should be done instead of the ROOR and HCl (which causes radical formation). The OH should be replaced with either a Cl, Br.
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Offline kiwi

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Re: Puzzling Benzene Transofrmation
« Reply #5 on: July 22, 2009, 04:32:55 AM »
the Freidel-Crafts acylation wouldn't give the product you've drawn; can you see why?
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Offline Heory

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Re: Puzzling Benzene Transofrmation
« Reply #6 on: July 22, 2009, 06:29:32 AM »
See the synthetic route as follows.
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Offline Ariana

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Re: Puzzling Benzene Transofrmation
« Reply #7 on: July 22, 2009, 05:00:18 PM »
Quote from: kiwi on July 22, 2009, 04:32:55 AM
the Freidel-Crafts acylation wouldn't give the product you've drawn; can you see why?

Not really o_O. Are you talking about step 7? Wouldn't it attach to the benzene at ortho or meta position?

Quote from: Heory on July 22, 2009, 06:29:32 AM
See the synthetic route as follows.

Wow. Thanks. It's much simpler. Though, I haven't used the reagent PPA before. Still *thumbs up*
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Offline nj_bartel

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Re: Puzzling Benzene Transofrmation
« Reply #8 on: July 22, 2009, 05:11:01 PM »
Hint about the Friedal Crafts - aluminum chloride has an empty p-orbital, which makes it a...?
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Offline kiwi

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Re: Puzzling Benzene Transofrmation
« Reply #9 on: July 24, 2009, 03:23:16 AM »
Quote
Not really o_O. Are you talking about step 7? Wouldn't it attach to the benzene at ortho or meta position?

Getting there - there are multiple problems with the step as drawn. Have a bit of think about the different reagents and functional groups in the SMs and product
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