Have lost the sheet with it on but can remember it:
Compound X reacts with water, toluene (presumably solvent) and heat to form para-chlorophenol.
Compound X has the following spectroscopic data:
C6H6OCl2, so HCl is eliminated in the reaction.
Contains fused 3 and 5 membered rings.
IR 1740 - suggests cyclopentanone ring
1H NMR:
d ~2.5ish (2H, dd, 15.4, 1.4 Hz) (1) - big geminal coupling indicates adjacent to pi system. Smaller coupling probably pseudo axial-pseudo equatorial
d ~2ish (2H, dd, 15.4, 4.3 Hz) (2) - big geminal coupling again. Small coupling probably the pseudo axial-pseudoaxial. Smaller than normal axial-axial as not anti to each other.
d ~1.5ish (2H, dd, 4.3, 1.4 Hz) (3)
These data fit with having the cyclopropane ring in a pseudoequatorial position relative to the 5M ring.
13C NMR
208 (s)
73 (s)
Two more peaks which I can't remember the precise chemical shifts. Both were low (alkyl), one doublet and one triplet.
Propose a structure for X and a mechanism for the reaction.
I think I've got a structure for X but have no idea for the mechanism.
Genuinely no idea.