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Topic: Stepwise conversion from benzene to benzoic acid  (Read 10913 times)

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Offline gralla55

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Stepwise conversion from benzene to benzoic acid
« on: April 28, 2010, 07:41:50 PM »
Which reagents are needed for step 1,2 and 3 (?) of the conversion from benzene to benzoic acid?

There are some samples in my textbook where they start with Br2, so I'm assuming A is correct for step 1. For step 2 maybe Mg to remove the Br, so D? And Then there would be needed some H I think so G for step 3. Any help? Thanks.

Offline g-bones

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Re: Stepwise conversion from benzene to benzoic acid
« Reply #1 on: April 28, 2010, 10:14:05 PM »
I believe your reagents are correct.  it is best to think of the step in which Mg is incorporated as not to remove Bromine but to create a particular reagent.  Can you think of what kind of reagent this might make and how it might interact with carbon dioxide?  the resulting product will be in basic form (again a result of the type of reagent Mg makes in combination with an aryl bromide) and thus your product must be obtained through treatment with an acid.  It would be best if you drew out the mechanism of each step to help you visualize the need for the next reagents.  Hope this helps!

Offline Doc Oc

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Re: Stepwise conversion from benzene to benzoic acid
« Reply #2 on: April 28, 2010, 11:49:45 PM »
For what it's worth, determining the step here with the Mg and the aryl halide will help you answer the question relating to deuterium.

Offline gralla55

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Re: Stepwise conversion from benzene to benzoic acid
« Reply #3 on: April 28, 2010, 11:54:55 PM »
Allright, I will try some more. Thanks guys!

Offline Doc Oc

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Re: Stepwise conversion from benzene to benzoic acid
« Reply #4 on: April 29, 2010, 08:31:36 AM »
Just a little help, the reaction of alkyl halides and Mg is named after someone, so look for a named reaction.

Offline discodermolide

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Re: Stepwise conversion from benzene to benzoic acid
« Reply #5 on: July 10, 2010, 09:44:39 AM »
Which reagents are needed for step 1,2 and 3 (?) of the conversion from benzene to benzoic acid?

There are some samples in my textbook where they start with Br2, so I'm assuming A is correct for step 1. For step 2 maybe Mg to remove the Br, so D? And Then there would be needed some H I think so G for step 3. Any help? Thanks.

Brominate benzene, then do a Fe catalysed Kumada coupling with MeMgBr, then oxidise the methyl group. 3 steps high yield.
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