pandalove89

7+ Year Member
Jun 15, 2011
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Which compound will dissolve in concentrated HBr or HCl but not in water?

a) octanal
b) 2-octanone
c) 2-octanamine
d) 1,2 - diethylbenzene
e) 2- octanol

I thought it as d) because benzene isn't soluble in water but the answer is c). Why? :mad:
 

hplfe

5+ Year Member
Jul 13, 2011
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because amines longer than 3 carbons long aren't water soluble. I guess its just one of those things that you have to memorize
 

Dew517

10+ Year Member
Dec 12, 2009
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So in these types of problems, just follow one rule: Acids dissolve bases, and bases dissolve acids.

The only base that is in the list is C. The strong acid will protonate the amino group and will bring it into the aqueous layer thereby dissolving it

D is not base and will not be dissolved in acid. Also C is definitely insoluble in water because of the 8 carbon chain.
 
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pandalove89

7+ Year Member
Jun 15, 2011
91
0
Status
Pre-Dental
So in these types of problems, just follow one rule: Acids dissolve bases, and bases dissolve acids.

The only base that is in the list is C. The strong acid will protonate the amino group and will bring it into the aqueous layer thereby dissolving it

D is not base and will not be dissolved in acid. Also C is definitely insoluble in water because of the 8 carbon chain.

Isn't that a bit counter intuitive? I thought aldehydes and ketones were acidic..?
 
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