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Topic: Mechanism  (Read 2797 times)

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Offline choupi

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Mechanism
« on: September 19, 2012, 11:21:50 PM »
Trying to figure out a problem by my professor through a mechanism. Could anyone just verify that what I did is right?
http://imgur.com/RQxH6
Thanks so much !
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Offline discodermolide

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Re: Mechanism
« Reply #1 on: September 19, 2012, 11:35:14 PM »
As far as I can tell it looks OK.
Remember and add the resonance contribution of the aromatic pi electrons to the aromatic carbocation.
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Offline synthon

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Re: Mechanism
« Reply #2 on: September 20, 2012, 10:01:01 AM »
What's going on with the Cl2 there?  Some shorthand I'm unaware of?
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Offline kirushanth

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Re: Mechanism
« Reply #3 on: September 20, 2012, 02:21:10 PM »
Quote from: synthon on September 20, 2012, 10:01:01 AM
What's going on with the Cl2 there?  Some shorthand I'm unaware of?
After the compound with the two rings are formed, the Cl2/AlCl3 mono-chlrorinates the phenyl group. Is cyclopentane ortho para directing or deactivating?(Looking at the final product, I presume it is an ortho para director)
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Offline discodermolide

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Re: Mechanism
« Reply #4 on: September 20, 2012, 02:35:29 PM »
Alkanes are ortho/para directors. Although in this case I would assume the major product is para due to the steric bulk of the cyclopentane ring.
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Offline synthon

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Re: Mechanism
« Reply #5 on: September 20, 2012, 03:05:31 PM »
Quote
the Cl2/AlCl3 mono-chlrorinates the phenyl group

I meant in regard to the mechanism, I guess this step was not asked to be drawn? 
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Offline kirushanth

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Re: Mechanism
« Reply #6 on: September 24, 2012, 02:06:30 PM »
The electrophilic aromatic substitution is actually well known.
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