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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: KSUPaintballa on April 19, 2010, 12:03:12 PM

Title: Why is salicylic acid solid at room temp while methyl salicylate is liquid?
Post by: KSUPaintballa on April 19, 2010, 12:03:12 PM

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

Title: Re: Why is salicylic acid solid at room temp while methyl salicylate is liquid?
Post by: MissPhosgene on April 19, 2010, 07:08:48 PM

Think H-bonding and you will get it.

Title: Re: Why is salicylic acid solid at room temp while methyl salicylate is liquid?
Post by: KSUPaintballa on April 20, 2010, 02:20:43 PM

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?

Title: Re: Why is salicylic acid solid at room temp while methyl salicylate is liquid?
Post by: MissPhosgene on April 20, 2010, 08:13:14 PM

Yes. The carbonyl of a carboxylic acid is a hydrogen bond acceptor and the -OH of a carboxylic acid is a hydrogen bond donor.