When (1-methylcyclopentyl) methanol is treated with H$$^+$$ at high temperature, it is converted to 1-methyl-1-cyclohexene.

IIT-JEE 2005 Mains Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 1

Therefore, X is 1-methyl-1-cyclohexene.

The mechanism for the same is represented below.

IIT-JEE 2005 Mains Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 2

The H$$^+$$ on heating with (1-methylcyclopentyl) methanol get attached to O atom of hydroxy group, producing a positive charge on O atom. The elimination of water molecule results in the formation of primary carbocation, which undergoes ring expansion followed by elimination of proton yields product X.

The 1-methyl-1-cyclohexene undergoes ozonolysis followed by treatment with Zn/ CH$$_3$$COOH, it gives 6-oxoheptanal.

IIT-JEE 2005 Mains Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 3

Therefore, compound Y is 6-oxoheptanal

IIT-JEE 2005 Mains Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 4

Y on further undergoes aldol condensation reaction to form $$\alpha$$, $$\beta$$ unsaturated carbonyl compounds in presence of NaOH followed by heat.

Final Answer

IIT-JEE 2005 Mains Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 5

Hints :

Ozonolysis of an unsaturated compound results in replacing double bonds with carbonyl group. The Zn in acetic acid is a reducing agent.

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