An organic acid P $$\left( {{C_{11}}{H_{12}}{O_2}} \right)$$ can easily be oxidized to a dibasic acid which reacts with ethylene glycol to produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products. P undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes another set of reactions to produce S.



The compound R is

Treatment of benzene with $$CO/HCl$$ in the presence of anhydrous $$AlC{l_3}/CuCl$$ followed by reaction with $$A{c_2}O/NaOAc$$ gives compound $$X$$ as the major product. Compound $$X$$ upon reaction with $$B{r_2}/N{a_2}C{O_3},$$ followed by heating at $$473$$ $$K$$ with moist $$KOH$$ furnishes $$Y$$ as the, major product. Reaction of $$X$$ with $${H_2}/Pd$$-$$C,$$ followed by $${H_3}P{O_4}$$ treatment gives $$Z$$ as the major product.

The compound $$Y$$ is

Treatment of benzene with $$CO/HCl$$ in the presence of anhydrous $$AlC{l_3}/CuCl$$ followed by reaction with $$A{c_2}O/NaOAc$$ gives compound $$X$$ as the major product. Compound $$X$$ upon reaction with $$B{r_2}/N{a_2}C{O_3},$$ followed by heating at $$473$$ $$K$$ with moist $$KOH$$ furnishes $$Y$$ as the, major product. Reaction of $$X$$ with $${H_2}/Pd$$-$$C,$$ followed by $${H_3}P{O_4}$$ treatment gives $$Z$$ as the major product.

The compound $$Z$$ is

The reaction of compound $$P$$ with $$C{H_3}MgBr$$ (excess) in $${\left( {{C_2}{H_5}} \right)_2}O$$ followed by addition of $${H_2}O$$ gives $$Q.$$ The compound $$Q$$ on treatment with $${H_2}S{O_4}$$ at $${0^ \circ }C$$ gives $$R.$$ The reaction of $$R$$ with $$C{H_3}COCl$$ in the presence of anhydrous $$AlC{l_3}$$ in $$C{H_2}C{l_2}$$ followed by treatment with $${H_2}O$$ producess compound $$S.$$ [$$Et$$ in compound $$P$$ is ethyl group]

The reactions, $$Q$$ to $$R$$ and $$R$$ to $$S,$$ are