Oxidation of Phenylethanal: Does it Produce Benzoic Acid and React with PCl5?

[crays]

Hi guys, my teacher once told me that if there's a benzene with a side chain which has a carbon group (e.g. aniline or benzaldehyde or 3-phenylpropane) it will be oxidise into benzoic acid, no matter what it is.

So my question now is, does oxidising phenylethanal gives me benzoic acid? or say even longer side chain like hipuric acid, will it be oxidised into benzoic acid too?

Another small question is that, will PCl₅ react with a carbonyl say propanone?

Thanks a bunch =D

 

[crays]

Anyone can please give me an answer?

 

[chemisttree]

You can't even begin to answer this question unless you show some work. What oxidation conditions are you given?

BTW, http://en.wikipedia.org/wiki/Aniline" doesn't have a carbon side chain.