он COOH NH2 Neutral Slightly acidic Acidic Basic Dissolve all four compounds in organic solvent (ether or CH2C2) Extract with Na HCO3 (aq); a weaker base will react with carboxylic acid (acidic component), but NOT the phenol (slightly acidic). Separate Organic layer Water layer СОО"Na+ OH NH2 Conjugate base of acid Three components remain Extract with Na OH (aq): strong base will react with slightly acidic component phenol HCI соон Water layer Separate Organic layer Acid solid precipitate NH2 O Na+ NaCI Conjugate base of acidic phenol Two components remain Extract with HCI, will react with basic component amine HCI Organic layer Water layer Separate он NH3CI Phenol solid precipitate Neutral remains Conjugate acid of base NaCI Dry with drying agent Evaporate organic solvent Allow to dry NaOH NH2 + NaCI + H20 Base solid precipitate

Question

Draw a flow diagram similar to the figure attached for the seperation of benzoic acid, 4'-aminoacetophenone, and 1,4-dimethoxybenzene. Note that since none of these substances are phenols, the extraction step using NaOH can be omitted. Circle and label the functional groups in these three compounds and tell which are capable of intermolecular hydrogen bonding.

он
COOH
NH2
Neutral
Slightly acidic
Acidic
Basic
Dissolve all four compounds in organic solvent (ether or CH2C2)
Extract with Na HCO3 (aq); a weaker base will react with carboxylic acid
(acidic component), but NOT the phenol (slightly acidic).
Separate
Organic layer
Water
layer
СОО"Na+
OH
NH2
Conjugate base
of acid
Three components remain
Extract with Na OH (aq): strong base
will react with slightly acidic
component phenol
HCI
соон
Water
layer
Separate
Organic
layer
Acid
solid precipitate
NH2
O Na+
NaCI
Conjugate base
of acidic phenol
Two components remain
Extract with HCI, will react
with basic component amine
HCI
Organic
layer
Water
layer
Separate
он
NH3CI
Phenol
solid precipitate
Neutral remains
Conjugate
acid of base
NaCI
Dry with drying agent
Evaporate organic solvent
Allow to dry
NaOH
NH2
+ NaCI + H20
Base
solid precipitate

Image Transcription

он COOH NH2 Neutral Slightly acidic Acidic Basic Dissolve all four compounds in organic solvent (ether or CH2C2) Extract with Na HCO3 (aq); a weaker base will react with carboxylic acid (acidic component), but NOT the phenol (slightly acidic). Separate Organic layer Water layer СОО"Na+ OH NH2 Conjugate base of acid Three components remain Extract with Na OH (aq): strong base will react with slightly acidic component phenol HCI соон Water layer Separate Organic layer Acid solid precipitate NH2 O Na+ NaCI Conjugate base of acidic phenol Two components remain Extract with HCI, will react with basic component amine HCI Organic layer Water layer Separate он NH3CI Phenol solid precipitate Neutral remains Conjugate acid of base NaCI Dry with drying agent Evaporate organic solvent Allow to dry NaOH NH2 + NaCI + H20 Base solid precipitate

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