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A Student Allowed an Alcohol, 4-Penten-1-Ol, to React with Br2

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A student allowed an alcohol, 4-penten-1-ol, to react with Br2, expecting to observe a simple addition of Br2 to the double bond. Instead, she isolated a compound X that proved to have the formula C5H9OBr. The reaction mixture from which X was isolated was very acidic.
A student allowed an alcohol, 4-penten-1-ol, to react with Br<sub>2</sub>, expecting to observe a simple addition of Br<sub>2</sub> to the double bond. Instead, she isolated a compound X that proved to have the formula C<sub>5</sub>H<sub>9</sub>OBr. The reaction mixture from which X was isolated was very acidic. Using mechanistic reasoning, including the curved-arrow notation, propose a structure for compound X. Show your logic at every step of the way! Your answer should explain why the reaction mixture became acidic. Using mechanistic reasoning, including the curved-arrow notation, propose a structure for compound X. Show your logic at every step of the way! Your answer should explain why the reaction mixture became acidic.

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