A multicomponent reaction is a reaction where three or more reactants react ... then obtained (20.0 — Analytical Chemistry Chemistry Question
Nitrophenols: synthesis and physical properties
A multicomponent reaction is a reaction where three or more reactants react ... then obtained (20.0 mmol).
9.1 A partial scheme for the formation of the 2-nitrophenol starting from the nitronium ion NO2 + is proposed below. Draw the missing intermediates and products.
9.2 Give at least two products other than 2-nitrophenol and 4-nitrophenol that could explain the low yield.
Various characterizations of the 2-nitrophenol and 4-nitrophenol were performed:
9.3 Using the NMR data, determine which product (2-nitrophenol or 4-nitrophenol) corresponds to A and B. To justify your answer, interpret the NMR chemical shifts of the products.
Model Answer
corresponding proton.
9.4 Which interaction(s) between B and water can explain the higher solubility in comparison to A? Choose the correct answer(s).
Intermolecular hydrogen bonds
Intramolecular hydrogen bond
Electrostatic interaction
Van der Waals interactions
Covalent bond
Model Answer
Correct answer: Intermolecular hydrogen bonds
4-nitrophenol 4-nitrophenolate
B can develop hydrogen bonds with water molecules, which increases its solubility, while A develops more intramolecular hydrogen bonds.
To check the purity of A and B, a Thin Layer Chromatography (TLC) on silica was performed. The eluent is a mixture of pentane/diethylether (7:3 in volume). After visualization of the TLC using a UV light, the retention factor was calculated for the two spots (0.4 and 0.9).
9.5 Choose the correct statement(s).
A has a ☐lower or ☐higher retardation factor (Rf) than B on the TLC because:
Model Answer
Correct statements:
A has a higher retardation factor (Rf) than B on the TLC because:
9.6 Which is the color of a solution of 4-nitrophenol in neutral water? Choose the correct answer.
Blue Green Pink Purple Red Yellow
9.7 Choose the correct answer.
4-nitrophenol has a longer absorption wavelength than its conjugated base because its conjugation is more important.
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Model Answer
9.9 pH = pKa when = . Using the figure above, we find pKa = 7.2.
9.10 Which alternative method(s) can be used for the titration of 4-nitrophenol? Choose the correct answer(s).
UV-Visible spectroscopy
Potentiometry
NMR
Conductometry
Model Answer
9.10 Correct answers:
UV-Visible spectroscopy, NMR, conductometry.