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JEE Advance - Chemistry (2017 - Paper 2 Offline - No. 3)

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 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 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 product $$S$$ is
JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 59 English Option 1
JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 59 English Option 2
JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 59 English Option 3
JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 59 English Option 4

Explanation

(i) Compound P reacts with $\mathrm{CH}_3 \mathrm{MgBr}$ in excess in $\left(\mathrm{C}_2 \mathrm{H}_5\right)_2 \mathrm{O}$ followed by addition of water to form alcohol derivative of the compound.

JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 59 English Explanation 1
(ii) Compound $Q$ undergoes dehydration in presence of $\mathrm{H}_2 \mathrm{SO}_4$ at $0^{\circ} \mathrm{C}$.

JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 59 English Explanation 2
(iii) Compound $R$ undergoes acylation of aromatic ring in presence of JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 59 English Explanation 3 and anhydrous $\mathrm{AlCl}_3$.

JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 59 English Explanation 4
The substitution should take place at ortho or para position but due to steric crowding at ortho and occupancy of para position. Meta position is substituted with acetyl group.

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