[wavefunction91]

Hey guys,

I've been looking at the question for 2 days now, I can't come up with an answer. I know that the scenario is mildly amusing..

"Mary Beth is over fraught because she just tried to carry out the following chemical extraction with the compounds shown below as members of the mixture she was working with:

Benzanoic Acid
Phenyl 4-methylhexaoate

Initaially there was 1g of each compound present in the mixture. She used 1.0 F NaOH to treat the mixture. She applied heat to the solution to speed the process along. She then allowed the solution to coll and extracted the aqueous solution with ether. After she treated the aqueous with HCl, she was astounded by the quantity of Benzanoic acid she recovered. She had much more than she had calculated there would be. Explain this."

I'm at a loss.. any help would be appreciated.

David Williams
ACS Tutor

[Doc Oc]

What the hell?  How old is this problem?  Benzanoic acid?  1.0 F NaOH?

Draw the structure of phenyl-4-methyl hexanoate.  Show what happens when it is exposed to hydroxide anion.