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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: w.uzar on March 07, 2021, 05:25:57 PM

Title: Problem witch Birch reduction
Post by: w.uzar on March 07, 2021, 05:25:57 PM

The reaction of anisole gives a 1-methoxycyclohexa-1,4-diene as a product of the birch reduction.

Could someone help me with the following issues and outline the reaction mechanisms?

1) Why does a 1-methoxycyclohexa-1,4-diene reaction with an acid that does not contain a nucleophilic anion give a 1-methoxycyclohexa-1,3-diene? What is the mechanism?

2) Why does a 1-methoxycyclohexa-1,4-diene reaction with an diluted acid give a cyclohex-3-en-1-one? What is the mechanism?

3) Why does a 1-methoxycyclohexa-1,4-diene reaction with an concentrated acid give a cyclohex-2-en-1-one? What is the mechanism?

Thank you very much for your answer!

Title: Re: Problem witch Birch reduction
Post by: rolnor on March 08, 2021, 08:32:25 AM

I give you a hint: Vinyl ether