1.00 g of acetophenone (120.15 g/mol) is warmed with excess iodine and 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.
of acetophenone () is warmed with excess iodine and sodium hydroxide. The equation is . Find the amount of acetophenone, the mass of iodoform () at a yield, and the number of carbon atoms in the organic acid that forms after acidification.
Need a reminder? The key ideaShow
Wolff-Kishner and Clemmensen turn C=O into CH (base and acid). Perkin: ArCHO, (CHCO)O and CHCOONa at 453 K give ArCH=CHCOOH. Haloform: CHCO- with 3 X and 4 NaOH gives CHX and the carboxylate with one carbon fewer. A crossed aldol with an aldehyde that has no alpha hydrogen is a Claisen-Schmidt reaction. For a gas, with kPa L/(mol K).
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. .
Step 2. Iodoform: .
Step 3. The acid. The methyl group leaves as iodoform. The rest is the benzoate ion, and acid turns it into benzoic acid, , with 7 carbons.
Answer: , and 7 carbons.
Check. Acetophenone has 8 carbons, and the acid has one fewer.
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