EasyChemistryHigh School (11–12)Organic Compounds with Functional Groups › Haloalkanes and HaloarenesNumerical
Aniline, 9.30 g, is dissolved in hydrochloric acid and cooled to 275 K…
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 dissolved in hydrochloric acid and cooled to . Sodium nitrite solution is added in the ratio of one mole of nitrite to one mole of aniline, and then the diazonium salt is warmed with copper(I) chloride in hydrochloric acid. Take the molar masses for aniline, for sodium nitrite and for chlorobenzene. The overall yield is . Find the amount of aniline, the mass of sodium nitrite and the mass of chlorobenzene obtained.
Need a reminder? The key ideaShow
A haloarene is made by ring halogenation, or from a diazonium salt: diazotisation with and HCl at to , then CuCl or CuBr (Sandmeyer), KI, or and heat. Isomers of a ring are counted by checking which patterns turn into each other by rotating or flipping the ring. Percent yield is .
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. Aniline. .
Step 2. Sodium nitrite. The ratio is , so .
Step 3. Theoretical chlorobenzene. .
Step 4. Obtained. .
Answer: of aniline, of sodium nitrite and of chlorobenzene.
Check. Nitrogen leaves as gas, so the product is lighter than the sum of the pieces. The yield of chlorobenzene in grams is less than the theoretical , as it should be.
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