2. Draw the 4 bromonium intermediates formed in the following reaction. On each, indicate which carbon(s) will be attacked by the nucleophilic methanol. + Br2 MeOH show the four bromonium intermediates and place a star (*) near the electrophilic Cs 3. Predict the products of the following reaction, including stereoisomers.

Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. LOCH3 LOCH3 HNO3 / CH3CO₂H O₂N • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. ● In cases where there is more than one answer, just draw one.

3. Both El and E2 reactions are possible with 3° alkyl halides. Which elimination mechanism would be favored by the base NaOH? Show the curved arrow mechanism leading to both regioisomers. Draw the energy diagram for this reaction and include the transition state structure leading to each of the possible products. Indicate which one would be favored and use the energy diagram to explain your reasoning. How would you favor the other regioisomer? Br z odd NaOH

Show how you would synthesize the target compound ne right from the starting compound on the left. Show reagents and conditions, and the structures of important intermediate compounds. Do not show any (arrow pushing) mechanism. Ignore stereochemistry in this question.