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Chemistry/Mpharm year 1 work (urgent help on resonance structures!)

I am confused, I've been asked to draw all the canonical resonance structures for 4-acetylphenol and 4-acetylphenolate, can anyone help me on this?

Reply 1

Original post
by 1iuy1iu
I am confused, I've been asked to draw all the canonical resonance structures for 4-acetylphenol and 4-acetylphenolate, can anyone help me on this?

To begin with, do you know what the structures of either of these are? i.e. could you draw skeletal formulae of either of them out without looking them up?

Additionally, how comfortable are you with curly arrow mechanisms? These are generally the most helpful way to think about accessible resonance forms.

Reply 2

Yes, reach out I'll help you

Reply 3

Original post
by TypicalNerd
To begin with, do you know what the structures of either of these are? i.e. could you draw skeletal formulae of either of them out without looking them up?
Additionally, how comfortable are you with curly arrow mechanisms? These are generally the most helpful way to think about accessible resonance forms.

I am currently unable to due to only being a month into the course. I have rewatched the lectures on resonance but no matter what I struggle to get the idea. To some extent, I get the mechanism.

Reply 4

Original post
by 1iuy1iu
I am currently unable to due to only being a month into the course. I have rewatched the lectures on resonance but no matter what I struggle to get the idea. To some extent, I get the mechanism.

Okay. If I told you an acetyl group is just a methyl group bonded to a carbonyl (e.g. CH3CO-), then you should hopefully be able to work out that 4-acetylphenol is just a benzene ring with a hydroxyl group on carbon 1 and an acetyl group on carbon 4. 4-acetylphenolate is the product formed when 4-acetylphenol reacts with a base (e.g. the phenol hydroxyl loses a H^+, so you get an anion CH3COC6H4O^-).

The trick for resonance forms is to try moving one double bond at a time and see which atoms end up picking up positive and negative charges. I think it would be sensible to start doing this with 4-acetylphenol and see what you can come up with.
(edited 3 months ago)

Reply 5

Original post
by TypicalNerd
Okay. If I told you an acetyl group is just a methyl group bonded to a carbonyl (e.g. CH3CO-), then you should hopefully be able to work out that 4-acetylphenol is just a benzene ring with a hydroxyl group on carbon 1 and an acetyl group on carbon 4. 4-acetylphenolate is the product formed when 4-acetylphenol reacts with a base (e.g. the phenol hydroxyl loses a H^+, so you get an anion CH3COC6H4O^-).
The trick for resonance forms is to try moving one double bond at a time and see which atoms end up picking up positive and negative charges. I think it would be sensible to start doing this with 4-acetylphenol and see what you can come up with.

I see, thank you very much.

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