Compound A with the formula C8H9N2O2Cl is insoluble in water and base. Compound A slowly dissolves i — Analytical Chemistry Chemistry Question
A chemical puzzle
Compound A with the formula C8H9N2O2Cl is insoluble in water and base.
Compound A slowly dissolves in a dilute solution of hydrochloric acid.
Which atom of A is involved in the reaction with HCl?
Model Answer
Nitrogen atom
Compound A readily reacts with acetyl chloride yielding a product which is insoluble in acid and base.
Which functional group(s) in A can account for the reaction with acetyl chloride?
Model Answer
–NH2 or –NHR
The 1H-NMR spectrum of A is shown in the figure:
[VISUAL]
Which groups can account for the signals a and b?
Model Answer
–CH2CH3
Which functional group is involved in the reaction with Sn/HCl?
Model Answer
–NO2
Draw the structure(s) of A that can be deduced on the basis of the information given. (Hint: Compound A does not react with a solution of silver nitrate, even not on heating.)
Model Answer
No AgNO3 reaction ⇒ no aliphatic chlorine substituent.
[VISUAL]
Possible structures of A are the isomers N-ethyl-2-chloro-4-nitroaniline and N-ethyl-3-chloro-4-nitroaniline.