PhCH=CHCH2CO-O-OCMe3 decomposes several 1000 times faster than MeCO-O-OCMe3 at rooom temperature. WHY?

Question

i think it's something to do with inductive or mesomeric effects and it may relate to radical chemistry.

Answer 1

Is the O-O-O supposed to be an epoxide ring or something?

Anyway, I'm pretty sure the answer to your question is resonance, just like 80% of all organic chem questions. The double bond and aromatic ring in the first compound help to stabilize an intermediate radical or positive charge on the carbon attached to the Oxygen chain. The methyl groups in the second compound don't do much to stabilize an intermediate.

Answer 2

Because the Hydrogen bonds are easier to break.