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Organic Chemistry - Caffeine Lab


Suzy Tran

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Hello I have a few problems with figuring out intermolecular forces between interactions of caffeine and water/ caffeine and methylene chloride (DCM) for my lab. Here are the questions:

 

  1. Identify and discuss two different structural features that would account for solubility in methylene chloride (hint: think intermolecular forces).
  2. Identify (circle on your structure) and discuss two different structural features that would account for solubility in water (hint: think intermolecular forces).

I attempted the problems and think that London dispersion forces are in between the caffeine and DCM interactions but not in the caffeine & water interactions because caffeine and water are already polar. Also, another interaction between caffeine & DCM is dipole-induced-dipole because DCM is nonpolar and is being induced by a polar compound (caffeine). For caffeine & water, I think that there is hydrogen bonding involved because the oxygens on caffeine (a part of the amide group) can interact with water for hydrogen bonding. However, I'm unsure with my answers and not sure what structural features go along with what I said especially for the interactions between caffeine and DCM.

 

Thank you for those that take the time to help!

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According to my TA, there are London Dispersion but I'm unsure if both of caffeine/DCM and caffeine/water interactions go through them as the dominant interaction. In DCM, I'm pretty sure there are dipole moment between Carbon and Chlorine. One chlorine is pointing up and the other one is pulling more downwards, these two dipole moments doesn't cancel each other out so it makes DCM kind of/ partially polar. For the other interactions between water and caffeine, well there's definitely london dispersion and hydrogen bonding, I'm not sure what else so I guess those are the two for water/caffeine interactions. I guess now I'm not 100% sure about caffeine/DCM interactions. Thanks BabcockHall.

Edited by Suzy Tran
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