Why Did the 2,4-DNPH Test Fail for Trans-p-anisalacetophenone?

[daselocution]

Hey all,

The other day in O-Chem lab I tested trans-p-anisalacetophenone with the 2,4-dinitrophenylhydrazine test. I did not get the positive result that I expected. Is there any way someone could help me rationalize this? Would it have to do with the aromatic group in my compound? Did I screw up in isolating the product? Should I have theoretically gotten a positive result?

thanks for your help

 

[DrDu]

http://de.scribd.com/doc/89231812/Synthesis-of-Trans-p-Anisalacetophenone

So apparently it should work.