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.
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