[Experimental11]

I received a contaminated mixture of 10 g anisole, 2 g benzoic acid and .2 g fluorenone.

To separate them, I dissolved in 20 ml methyl tbu ether, did 2x extractions with 10 ml NaOH. Added HCl until litmus paper turned blue to red, and vacuum filtered to get benzoic acid. My percent yield was around 60 percent.

Then I took the organic solution, dried with drying agent, and distilled. Did not collect the 50 degree distillate and first few drops at 155 degrees c bc it might contain ether, but my percent yield of anisole was around 50%.

Where did all my reagants go? Why was I so far from 100% yield?

[Babcock_Hall]

Would you mind making a few suggestions concerning what you think might be the reasons?  Then we could comment on those ideas.