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CHEM 2364- Experiment 1

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acid-base extraction - Answer A liquid-liquid extraction that is based on the neutral/acidic/basic properties of compounds How is the acid base extraction performed? - Answer Using 2 immiscible solvents, one is aqueous (water) and the other one organic (DCM or ethyl acetate) Can a compound that is soluble in water be used in an acid base extraction? - Answer No Non-polar compounds insoluble in water: - Answer hexane, benzene, carbon tetrachloride, alkyl halides, nitrocompounds, and ethers The organic solvent (layer or phase): - Answer must be water insoluble, have a low boiling point (DCM and Ethyl Acetate) DCM - Answer CH2Cl2 Dichloromethane Denser than water Ethyl Acetate - Answer EtOAc CH3CO2CH2CH3 Less dense than water The aqueous solvent (layer or phase): - Answer - Aqueous acid: HCl in case the compound to extract is basic -- amines - Aqueous base: NaHCO3 in case the compound to extract has a pka lower than 6 -- carboxylic acids - Aqueous base: NaOH in case the compound to extract has a pka lower than 15 -- carboxylic acid and phenol The acidity of halocarboxylic acids increases with...and decreases with - Answer - the electronegativity of the halogen - the distance of the halogen to the carboxylic acid group The liquid-liquid extraction is performed in what type of funnel? - Answer separatory funnel Gravity filtration - Answer 1. fold filter paper

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CHEM 2364- Experiment 1
acid-base extraction - Answer A liquid-liquid extraction that is based on the
neutral/acidic/basic properties of compounds



How is the acid base extraction performed? - Answer Using 2 immiscible solvents, one is
aqueous (water) and the other one organic (DCM or ethyl acetate)



Can a compound that is soluble in water be used in an acid base extraction? - Answer No



Non-polar compounds insoluble in water: - Answer hexane, benzene, carbon tetrachloride,
alkyl halides, nitrocompounds, and ethers



The organic solvent (layer or phase): - Answer must be water insoluble, have a low boiling
point (DCM and Ethyl Acetate)



DCM - Answer CH2Cl2

Dichloromethane

Denser than water



Ethyl Acetate - Answer EtOAc

CH3CO2CH2CH3

Less dense than water



The aqueous solvent (layer or phase): - Answer - Aqueous acid: HCl in case the compound to
extract is basic --> amines

- Aqueous base: NaHCO3 in case the compound to extract has a pka lower than 6 --> carboxylic
acids

- Aqueous base: NaOH in case the compound to extract has a pka lower than 15 --> carboxylic
acid and phenol



The acidity of halocarboxylic acids increases with...and decreases with - Answer - the
electronegativity of the halogen

- the distance of the halogen to the carboxylic acid group



The liquid-liquid extraction is performed in what type of funnel? - Answer separatory funnel

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