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Topic: Modification of Riemer Tieman reaction  (Read 3674 times)

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Offline harini_5

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Modification of Riemer Tieman reaction
« on: May 05, 2008, 11:02:16 AM »
I’ve learnt about the modification of Riemer Tieman reaction in which carbon tetra chloride is added to phenol to get aromatic acids. What is the electrophile attacking phenol? 

Offline macman104

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Re: Modification of Riemer Tieman reaction
« Reply #1 on: May 05, 2008, 12:23:34 PM »
Are you saying that phenol would create benzoic acid, or it would it create 2 (or 4)-hydroxybenzoic acid?  As it stands, I'm not entirely sure about this mechanism.  You learned about this in your course, or you read it, or...

Offline harini_5

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Re: Modification of Riemer Tieman reaction
« Reply #2 on: May 06, 2008, 01:49:13 PM »
Sorry for not stating clearly  ::) What I meant was when carbon tetrachloride is added to phenol we get p-hydroxy benzoic acid as the major product.

Offline Yarr

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Re: Modification of Riemer Tieman reaction
« Reply #3 on: May 07, 2008, 06:14:26 AM »
Phenol can be not only O-alkylated but also C-alkylated, with the para position being the most reactive. This introduces a -CCl3 group in para position, which on hydrolysis gives the -COOH group.

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