AAMC 4 orgo q

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2010premed

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The solubility data indicate that compound C most likely contains which of the following functional groups?


  • Carboxylix acid and amide
  • Amine and amide
  • Amide and nitro
  • Amine and carboxylic acid

Compound C is soluble in both dilute acid and base… What is the background knowledge that I should have here?

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If you protonate a base, you turn it into a positive ion, which is more likely to be water soluble. If you deprotonate an acid, you turn it into a negative ion, which is more likely to be water soluble. Thus, weak organic acids (like carboxylic acids) are more water soluble in basic solutions, while weak organic bases (like amines) are more water soluble in acid solutions.
 
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I'm assuming that since you see that the question has to do with acids and bases, you have to look for the functional groups that have acidic and basic properties.

Only carboxylic acid and amines do.

Is this way of thinking the right approach to this problem?
 
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