Destroyer Organic Chemistry Question 149

[Kstar007]

The answer key states c) 2-octanamine will not dissolve in water because "amines larger than three carbons will not be water soluble". Wouldn't the same be true e- 2-octanol and the vanderwall forces dominate the h-bonding because it also has more than 3 carbons?

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[DAT Destroyer]

The answer key states c) 2-octanamine will not dissolve in water because "amines larger than three carbons will not be water soluble". Wouldn't the same be true e- 2-octanol and the vanderwall forces dominate the h-bonding because it also has more than 3 carbons?

This is an important problem,, and you missed a key point. All these molecules are water insoluble BUT...when acid is added, it protonates the amine and makes it into the IONIC ammonium ion,,,,,which is water soluble since it now has a charge. REMEMBER,,,,,amines are bases.....and when protonated they become water soluble. This is the basis for doing an extraction in lab to separate an amine from a complex mixture. Hope this helps.

 

[Kstar007]

Got it, that really helped. Thanks for the explanation!