Can someone draw what the missing structure is? I can't find it.
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$\begingroup$ If someone could find the resonance structures of phenol in a book or online, could you upload it? I want to compare my answers for that too. $\endgroup$– yolo123Sep 21, 2014 at 15:07
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2$\begingroup$ It seems you didn't draw the thiol group ($\ce{-SH}$) in any of your canonical structures, which is why some are missing. Remember that the sulphur atom has non-bonding pairs next to a $\pi$-conjugated system. What can this mean? $\endgroup$– Nicolau Saker NetoSep 21, 2014 at 15:15
1 Answer
The missing resonance structure is
If you replace "SH" with "OH" in the 4 structures you've drawn (your 5th structure is the same as the one pictured on the exam) and the one I've drawn, you'll have all of the analogous resonance structures for phenol.
EDIT : response to OP's comment
In my view, it doesn't really matter how you order the structures, but your suggestion (between the 3rd and 4th structures from the left) seems logical. I've redrawn the figure to show the electron movement.
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$\begingroup$ Perfect! Ron, I still have a question, where should I include this resonance structure? My teacher wants to see the electron pushing. Say I were to put your structure between the THIRD and FOURTH ORGANIC STRUCTURE FROM LEFT, would I have to resend the electrons originally on the sulfur atom to the sulfur atom and then transport the double bond onto the + charge formed? $\endgroup$– yolo123Sep 21, 2014 at 15:23
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$\begingroup$ yolo123, I've edited my post to address your comment, let me know if you still have questions. $\endgroup$– ronSep 21, 2014 at 15:34