[curiouscat]

If I reacted 2-Phenyloxirane (A) with HCl I expect I'll form 2-Chlor-1-phenylethanol (B).  Am I right in expecting this?

(A)


(B)


If so would 2-Phenyloxirane (A) also be expected to react with HNO3 and Acetic Acid? I think not; but wanted to check.

[discodermolide]

If you react it with HCl it will protonate the oxygen atom. The epoxide ring opens to give the benzylic cation which is resonance stabilised through the aromatic ring. The chloride will add to the benzylic position. So you will get the 2-chloro-2-phenylethanol.
I don't see what you are getting at with the HNO₃ and acetic acid.

[curiouscat]

I don't see what you are getting at with the HNO₃ and acetic acid.

Thanks. Sorry, I should have explained why.

I've a situation where we want to temporarily acidulate a solution of  2-Phenyloxirane. Unfortunately, using HCl fails; we lose significant amounts of 2-Phenyloxirane (presumably via 2-chloro-2-phenylethanol ).

I was trying to reason if HNO3 and acetic acid were safer choices. If not which other acids to try.

[discodermolide]

Try camphor sulphonic acid to para-toluenesulphonic acid.

[curiouscat]

Try camphor sulphonic acid to para-toluenesulphonic acid.

Ok. Thanks for the tip. I will. 

You think HNO3 / AcOH might damage 2-Phenyloxirane? What might they form. Just curious.

[discodermolide]

Don't really know. I guess it will open the ring and then perhaps get oxidised. Or the ring may get nitrated?