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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: metallica00789 on May 04, 2013, 10:16:55 PM

Title: Butylated hydroxytoluene and radical reaction
Post by: metallica00789 on May 04, 2013, 10:16:55 PM

Hi,
One of my online homework is to predict structure of the radical when Butylated hydroxytoluene reacts with radical R..
I draw the following structure as the structure of the radical but it seems wrong
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fs21.postimg.org%2Fwqmimhlhz%2FRadical.jpg&hash=00c781cc973e8eb53b4fbbac2c524e4216c1d0c3)
I thought that the radical will attack the the terminal -CH3 and the resonance will favor my product structure because it is a tertiary radical.
Any hints?
Thank you

Title: Re: Butylated hydroxytoluene and radical reaction
Post by: orgopete on May 05, 2013, 09:25:44 AM

The methyl and t-butyl groups help stabilize forms of the product radical.