Basically our experiment was that wewere given a unknown solid (mixture) contain

Question

Basically our experiment was that wewere given a unknown solid (mixture) containing three compounds
it was known that my compounds were

phenanthrene, methyl 4-aminobenzoate, & 1,4-dibromobenzene

basically when I extracted the two compounds and rid of that impurity (1,4-dibromobenzene) I got low percent yields

For example I got

the theoretical yield for phenanthrene in the mixture was 0.499 grams but only 0.139 grams was obtained at the conclusion of the extraction.   This resulted in a rather low percent yield of 27.9%.  

my substance is indeed phenanthrene (really close melting point range compared to the literature value) but I simply got low amounts compared to the theoretical yield

What are some speific reasons why

my professor wants in my report...
"Don

Explanation / Answer

You reextract the organic layer for three times again and see anything is staying there. or check the TLC of the aqueous layer alone, did you see any spots in polar region.

or you can collect the 1,4-dibromo benzene and see the quantity

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