Aniline, 4.65 g, is warmed with an excess of acetic anhydride, (CH₃CO)₂O…
Contributed by StemPy LabTry it on paper first. A hint, the key idea and the worked solution are here when you need them.
Aniline, , is warmed with an excess of acetic anhydride, . The products are acetanilide and acetic acid. Use C = 12, H = 1, N = 14 and O = 16 in g/mol, so aniline is , acetanilide is and acetic acid is . Find the amount of aniline. Find the mass of acetanilide at a yield of 100 %. Then find the mass collected at a yield of 80 %. Last, find the mass of acetic acid formed at a yield of 100 %.
Need a reminder? The key ideaShow
The amine lone pair attacks carbon atoms that are short of electrons. Primary and secondary amines are acylated. Only primary amines give the carbylamine reaction. Nitrous acid gives nitrogen gas with a primary aliphatic amine. At 273 K and 1 atm, one mole of gas has a volume of . Hinsberg's reagent gives an alkali-soluble sulphonamide with a primary amine, an insoluble one with a secondary amine and no product with a tertiary amine.
The worked solution
Have you tried it?
Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.
Step 1. Amount. .
Step 2. Acetanilide at 100 %. .
Step 3. At 80 %. .
Step 4. Acetic acid. .
Answer: , , and .
Check. The masses balance: of reactants (acetic anhydride is ), and of products.
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