Organic Lab (I) Expt 5: Extraction with acid and base

For the three compounds in the mixture sample, which will mainly remain in the organic layer no matter the aqueous layer is acidic or basic?

• 4-Methylanisole

• 4-Methoxyphenol

• 4-Chloroaniline

• All compounds will dissolve in the aqueous layer

Which compound in the sample mixture will dissolve in the aqueous layer when the aqueous layer is acidic?

• All compounds will not dissolve in acidic aqueous layer

• 4-Chloroaniline

• 4-Methylanisole

• 4-Methoxyphenol

Which compound in the sample mixture will dissolve in the aqueous layer when the aqueous layer is basic?

• All compounds will dissolve in basic aqueous layer

• 4-Chloroaniline

• 4-Methylanisole

• 4-Methoxyphenol

Which compound in the sample mixture is the most acidic?

(With lowest pK_a value)

• 4-Methoxyphenol

• 4-Chloroaniline

• 4-Methylanisole

• Dichloromethane

Which compounds in the sample mixture can potentially act as a Lewis base?

(Hint: lone pair electrons)

• 4-Methylanisole

• 4-Chloroaniline

• 4-Methoxyphenol

• None