January 17, 2022, 11:04:09 AM
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Topic: Why is salicylic acid solid at room temp while methyl salicylate is liquid?  (Read 17094 times)

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Offline KSUPaintballa

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I have to answer this question for my lab.  I'm thinking that there is electron delocalization in the carboxylic acid group of salicylic acid and this stabilizes the molecule, where as in methyl salicylate there is less delocalization of electrons because the methyl group is electron donating.  Any help you could provide would be much appreciated!

Thanks!
Matthew

Offline MissPhosgene

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Think H-bonding and you will get it.
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Offline KSUPaintballa

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ok, so I'm not getting it.  Does salicylic acid hydrogen bond to other salicylic acid molecules, and that's why it is solid at room temp?

Offline MissPhosgene

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Yes. The carbonyl of a carboxylic acid is a hydrogen bond acceptor and the -OH of a carboxylic acid is a hydrogen bond donor. 
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

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