What is shown below is an interesting way of making lactone B from lactone A. The reaction takes place when A is treated with sodium hydride, a strong base, which deprotonates the OH group. Draw a curved arrow mechanism which explains how B is formed. The reaction takes place in multiple steps. Show all curved arrows, relevant lone pairs, and formal charges. (7 p) OH H = A Br NaH H [strong base] H B

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