Butanamide, C₃H₇CONH₂, is warmed with bromine and aqueous sodium hydroxide…
Contributed by StemPy LabTry it on paper first. A hint, the key idea and the worked solution are here when you need them.
Butanamide, , is warmed with bromine and aqueous sodium hydroxide. The product is propan-1-amine. A chemist uses of the amide and collects the amine in a yield of . Use C = 12, H = 1, N = 14 and O = 16 in g/mol. Find the amount of amide, the mass of amine at a yield of 100 %, and the mass the chemist collects. Then find how many moles of sodium hydroxide are needed for the amount of amide, from the equation in the key idea.
Need a reminder? The key ideaShow
The nitro group, the nitrile group and the amide group are reduced to a primary amine. A nitrile adds one carbon to the halide it came from. The Hofmann bromamide degradation removes one carbon: . The Gabriel synthesis makes pure primary aliphatic amines.
The worked solution
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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. Molar masses. Butanamide: . Propan-1-amine: .
Step 2. Amount of amide. .
Step 3. Amine at 100 %. One mole of amide gives one mole of amine: .
Step 4. Amine collected. .
Step 5. Sodium hydroxide. The equation uses 4 mol of NaOH for each mol of amide: .
Answer: , , and of NaOH.
Check. The amine has one carbon fewer than the amide, which is why its molar mass is lower by 28 g/mol.
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