A derivative of toluene ( X ) is treated with Cl 2 in the presence of UV light until a specific mass increase is observed. Subsequent treatment with boiling water and CaCO 3 yields p -methoxybenza

Question

A derivative of toluene ( X ) is treated with Cl 2 ​ in the presence of UV light until a specific mass increase is observed. Subsequent treatment with boiling water and CaCO 3 ​ yields p -methoxybenzaldehyde. If the chlorination was stopped after exactly two moles of Cl 2 ​ reacted per mole of ( X ) , which of the following is true?

TestHub · Accepted Answer

Concept: Free radical halogenation, gem-dichloride hydrolysis, and buffering in organic synthesis.

Solution:

(X) is p-methoxytoluene. Radical chlorination at the benzylic position yields p-CH₃OC₆H₄CHCl₂. Hydrolysis of gem-dichlorides gives a gem-diol, which loses water to form an aldehyde. CaCO₃ is used to remove HCl to prevent ether cleavage or polymerization.

Final Answer: Option (C)

Chemistry - Carbonyl compounds Question with Solution | TestHub

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