This problem is adapted from an experiment designed for undergraduate
(a) Reaction of (E)-1-(p-methoxyphenyl)propene with m-chloroperoxybenzoic acid converted the
(b) Assign the signals in the 1H NMR spectrum of the epoxide to the appropriate hydrogens.
δ 1.4 (doublet, 3H) δ 3.8 (singlet, 3H)
δ 3.0 (quartet of doublets, 1H) δ 6.9 (doublet, 2H)
δ 3.5 (doublet, 1H) δ 7.2 (doublet, 2H)
(c) Three signals appear in the range δ 55–60 in the 13C NMR spectrum of the epoxide. To which carbons of the epoxide do these signals correspond?
(d) The epoxide is isolated only when the reaction is carried out under conditions (added Na2CO3) that ensure that the reaction mixture does not become acidic. Unless this precaution is taken, the isolated product has the molecular formula C17H17O4Cl.
Suggest a reasonable structure for this product and write a reasonable mechanism for its formation.
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