IIT-JEE 2010 · Paper 1 · Chemistry Q5

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ChemistrySingle correct+3 / -1Question 5 of 84

In the reaction $\ce{C6H5-OCH3 ->[HBr]}$ the products are

\ce{Br-C6H4-OCH3}

(para) and

\ce{H2}

\ce{C6H5Br}

and

\ce{CH3Br}

\ce{C6H5Br}

and

\ce{CH3OH}

\ce{C6H5OH}

and

\ce{CH3Br}

Answer and worked solution

Official answer: D

Cleavage of an aryl alkyl ether by HBr. The ether oxygen is protonated and bromide attacks the methyl carbon by $\mathrm S_\mathrm N2$ . Attack on the aromatic carbon is impossible ( $sp^2$ C, partial double-bond character of Ar-O).
$\ce{C6H5OCH3 + HBr -> C6H5OH + CH3Br}.$

(D)

Topics:Ethers

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IIT-JEE 2010 · Paper 1, Chemistry question 5