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Question

Which pair of products would result from the acid cleavage of phenyl propyl ether with excess concentrated HBr?

A
Phenol and 1-propanol
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B
Bromobenzene and 1-propanol
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C
Bromobenzene and 1-bromopropane
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D
Phenol and 1-bromopropane
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Solution

The correct option is D Phenol and 1-bromopropane
The cleavage of alkyl aryl ethers in presence of conc. HBr gives phenols and alkyl bromides.
Thus, the acid cleavage of phenyl propyl ether, in presence of conc. HBr gives phenol and 1-bromopropane.
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