Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presenc...

Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH3 forms compound A. A has a molecular ion in its mass spectrum at 154 and a strong peak in its IR spectrum at 1730 cm-1, in addition to C-H stretching absorptions. Without added NaOCOCH3, oxidation of citronellol with PCC yields isopulegone, which is then converted to B with aqueous base. B has a molecular ion at 152, and a peak in its IR spectrum at 1680 cm-1 in addition to C-H stretching absorptions.

a.          Identify the structures of A and B.

b.          Draw a mechanism for the conversion of citronellol to isopulegone.

c.           Draw a mechanism for the conversion of isopulegone to B.