Question

Click the "draw structure" button" to launch the drawing utility. 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. Draw the structures of A and B. A qsimage

Answer 1

Compound A= 3,7-dimethyl-6-octenal

Compound B= 3-methyl-6-(prop-1-en-2-yl)-1-en-cyclohexol

Step-by-step explanation:

For compound A we will have a redox reaction (PCC) in the citronellol the susceptible part to the oxidation is the alcohol group. Therefore this group would be converted into an aldehyde the molar mass of the product is 154.14 g/mol, so it fits with the mass spectrum info.

For compound B we will have an elimination reaction in which the OH remove an hydrogen from the molecule to produce a double bond near to the oxo group in the isopulegone to produce an enol. The molecule produced has a molar mass of 152.12 g/ mol so it fits with the mass spectrum info.