Try it on paper first. A hint, the key idea and the worked solution are here when you need them.
of toluene () reacts with chlorine in sunlight to give benzal chloride () in a yield of . The benzal chloride is hydrolysed with water at to give benzaldehyde () in a yield of . Find the amount of toluene, the mass of benzal chloride, the mass of benzaldehyde and the overall yield.
Etard: toluene, CrOCl in CS, then HO. Gattermann-Koch: benzene, CO, HCl, anhydrous AlCl and CuCl. Friedel-Crafts acylation: benzene, an acyl chloride and anhydrous AlCl, which is needed in a little more than one mole for each mole of acyl chloride. The overall yield of a route is the product of the step yields.
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. .
Step 2. Benzal chloride: .
Step 3. Benzaldehyde: .
Step 4. Overall yield , which is .
Answer: , , and .
Watch out. A second step cannot give back what the first step lost. Two good yields still give a lower overall yield.
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