Homework No.

3 – AMINES
(Min. 10 points – Max. 18 points)

1) Draw their structures and rank the following compounds in order of ascending basicity:
(a) 4-Nitroaniline, p-aminobenzaldehyde , 4-bromoaniline
(b) p-Chloroaniline, 4-aminoacetophenone, p-methylaniline
Explain your decision. (3 points)

2) Correctly number and name the following molecules. (2 points)

3) Draw equations of the following reactions and and explain to which direction is the respective quillibrium
shifted. (3 points)
a) cyclohexylamine + water
b) aniline + sulphuric acid
c) triethylamine + acetic acid
4) How might the following amines be prepared using reductive amination reactions? Suggest appropriate
substrates, reagents and conditions. Name all organic compounds. (4 points):

5) Write a complete reaction mechanism of ammonia with 4-fold excess of propyl iodide. Name all organic
intermediates and the final product. What is the type of reaction? (4 points)

6) Draw a detailed mechanism of reaction of ethyl phenyl ketone with benzylamine under the hydrogen
pressure in the presence of finely powdered nickel. (2 points)