Question

Acidic compound: Ethyl 4 aminobenzoate

Neutral compound: Fluorenone

(12 points). Separation Scheme:_(5 points for the aqueous extract or layer and 7 points for the organic extract or layer). By drawing the actual structures of the neutral compound that you have identified and either the acidic or basic compound or impurity present in your mixture, write a separation scheme for this binary mixture. Draw the appropriate complete structures with the correnct number of unshared electrons and/ or charges if any during each stage of the separation process, including the solvents and any other appropriate reagents that you may have employed to separate the two compounds. + structure of the acidic or basic compound structure of the neutral compound mixture of the two dissolved in diethyl ether solvent aqueous layer ether layer

Answer 1

Basic compounds amines are soluble in acid HCl and regenereted by base NaOH.

R-NH2 + HCl ----> R-NH3+ Cl-

Regeneration:
R-NH3+ Cl-. + NaOH ----> R-NH2 + NaCl + H2O

Weak acids (phenols are soluble in strong base NaOH and regenereted by acid HCl

R-OH + NaOH ----> R-ONa + H2O

Regeneration:
R-ONa + HCl ----> R-OH + NaCl

Strong acids carboxylic acids are soluble in weak base NaHCO3 and regenereted by acid HCl.

R-COOH + NaHCO3 ----> RCOONa + H2O + CO2

Regeneration:
RCOONa + HCl ----> RCOOH + NaCl

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