(Solved): 1. (5 points) The bromine test is a qualitative method used to detect unsaturation (i.e., carbon-c ...

1. (5 points) The bromine test is a qualitative method used to detect unsaturation (i.e., carbon-carbon double or triple bonds). In a positive test, the distinctive \( \mathrm{Br}_{2} \) color should dissipate as the reagent is consumed in the reaction. Provide the curved-arrow mechanism for the reaction between cyclohexene and \( \mathrm{Br}_{2} \). Reaction intermediates are provided. \( +: \ddot{\mathrm{Br}}={ }_{*}^{*} \mathrm{Br}_{*}^{*} \) 2. (6 points) Predict the major product of the following dehydration reactions. Be sure to account for regio- and stereochemistry in your answer. \( \frac{\mathrm{H}_{2} \mathrm{SO}_{4} / \mathrm{H}_{3} \mathrm{PO}_{4}}{\mathrm{EtOH} \text {, heat }} \) CHEM 237 Discussion Questions - Dehydration of Cyclohexanol 3. (4 points total) Using chemical structures, show why concentrated \( \mathrm{HCl} \) is a poor choice for the dehydration of cyclohexanol. (Hint: You should draw the full reaction scheme(s) and clearly depict the problem.)