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Topic: Use of lead tetra acetate in this reaction ??  (Read 3504 times)

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Offline ashish

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Use of lead tetra acetate in this reaction ??
« on: July 09, 2017, 10:45:43 AM »
here is the reaction

https://postimg.org/image/3nxt54hhz/

what could be the use of lead tetracetate ??

someone told me that COOH will be converted into COOCH3 ?? but then what will be the mechanism ??

Offline clarkstill

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Re: Use of lead tetra acetate in this reaction ??
« Reply #1 on: July 10, 2017, 10:04:00 AM »
someone told me that COOH will be converted into COOCH3 ?? but then what will be the mechanism ??

I'd forget about what they told you. Start off by considering that Pb(OAc)4 is lead in the +4 oxidation state, so it's a pretty strong oxidant. What do you think you'd get if you oxidized your starting material?

Offline ashish

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Re: Use of lead tetra acetate in this reaction ??
« Reply #2 on: July 12, 2017, 02:53:45 PM »
someone told me that COOH will be converted into COOCH3 ?? but then what will be the mechanism ??

I'd forget about what they told you. Start off by considering that Pb(OAc)4 is lead in the +4 oxidation state, so it's a pretty strong oxidant. What do you think you'd get if you oxidized your starting material?

here is my answer

https://postimg.org/image/47cwxfu03/

is the mechanism correct??
« Last Edit: July 12, 2017, 03:55:46 PM by Arkcon »

Offline Babcock_Hall

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Re: Use of lead tetra acetate in this reaction ??
« Reply #3 on: July 12, 2017, 03:09:33 PM »
Did you in fact oxidize your starting material?  Why or why not?

Offline ashish

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Re: Use of lead tetra acetate in this reaction ??
« Reply #4 on: July 13, 2017, 08:53:46 AM »
Did you in fact oxidize your starting material?  Why or why not?

yes....hydrogen is getting removed from benzene ring so it is oxidation

Offline Babcock_Hall

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Re: Use of lead tetra acetate in this reaction ??
« Reply #5 on: July 13, 2017, 09:32:25 AM »
What about the carbon atom in the carboxylate group?  Is it getting oxidized?

Offline ashish

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Re: Use of lead tetra acetate in this reaction ??
« Reply #6 on: July 13, 2017, 11:42:27 AM »
What about the carbon atom in the carboxylate group?  Is it getting oxidized?

i think its getting oxidised from +3 to +4

Offline clarkstill

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Re: Use of lead tetra acetate in this reaction ??
« Reply #7 on: July 13, 2017, 12:17:33 PM »
someone told me that COOH will be converted into COOCH3 ?? but then what will be the mechanism ??

I'd forget about what they told you. Start off by considering that Pb(OAc)4 is lead in the +4 oxidation state, so it's a pretty strong oxidant. What do you think you'd get if you oxidized your starting material?

here is my answer

https://postimg.org/image/47cwxfu03/

is the mechanism correct??

This looks pretty decent to me.

Offline Babcock_Hall

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Re: Use of lead tetra acetate in this reaction ??
« Reply #8 on: July 13, 2017, 04:09:29 PM »
What about the carbon atom in the carboxylate group?  Is it getting oxidized?

i think its getting oxidised from +3 to +4
I agree, and I agree about the mechanism also.

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