ochem question

[ak47]

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8. A compound is separated from an ethereal mixture by extraction with cold, aqueous NaHCO3, then recovered by addition of HCl to the extract. Which of the following is a likely identity of the compound?
A. CH3(CH2)7CH2OH
B. CH3(CH2)7CHO
C. CH3(CH2)7CH2NH2
D. CH3(CH2)7COOH
E. CH3(CH2)7COONa

answers is D. can someone break it down for me? thanks

 

[far123]

the best way to purify an organic acidic compound is to treat it with a dilute base of NaOH, or weak base like NaHco3. this will produce anionic salts of acidic compound, usually freely soluble in the aq. soln and can be removed from the organic compound
hope it helps